1-tert-butyl 2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

• ChemBase ID: 52597
• Molecular Formular: C11H19NO5
• Molecular Mass: 245.27226
• Monoisotopic Mass: 245.12632271
• SMILES: C(=O)([C@@H]1C[C@H](CN1C(=O)OC(C)(C)C)O)OC
• Canonical SMILES: COC(=O)[C@@H]1C[C@H](CN1C(=O)OC(C)(C)C)O
• InChI: InChI=1S/C11H19NO5/c1-11(2,3)17-10(15)12-6-7(13)5-8(12)9(14)16-4/h7-8,13H,5-6H2,1-4H3/t7-,8+/m1/s1
• InChIKey: MZMNEDXVUJLQAF-SFYZADRCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-tert-butyl 2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate
• IUPAC Traditional name: 1-tert-butyl 2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate
• Synonyms: (2S,4R)-1-tert-Butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate; (2S,4R)-1-(tert-Butoxycarbonyl)-4-hydroxy-2-(methoxycarbonyl)pyrrolidine; trans-1-(tert-Butoxycarbonyl)-4-hydroxy-L-proline methyl ester; 1-tert-Butyl 2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate; N-Boc-trans-4-hydroxy-L-proline methyl ester; Boc-Hyp-OMe; (2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl) 2-Methyl Ester; 1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S-trans)-1-tert-Butoxycarbonyl-4-hydroxypyrrolidine-2-carboxylic Acid Methyl Ester; (2S,4R)-1-Boc-4-hydroxy-L-proline Methyl Ester; Methyl (4R)-N-Boc-4-hydroxy-L-prolinate; N-tert-Butoxycarbonyl-L-hydroxyproline Methyl Ester; (2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic Acid 1-tert-Butyl Ester 2-Methyl Ester; N-Boc-反式-4-羟基-L-脯氨酸甲酯

Database IDs

• CAS Number: 74844-91-0
• MDL Number: MFCD00076981
• PubChem SID: 24883051; 162057360
• PubChem CID: 2734883

CALCULATED PROPERTIES

• Acid pKa: 14.790254
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.18424809
• LogD (pH = 7.4): 0.18424807
• Log P: 0.18424809
• Molar Refractivity: 59.1464 cm^3
• Polarizability: 23.672804 Å^3
• Polar Surface Area: 76.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMF; Ethyl Acetate
• Apperance: Clear Colourless Oil
• Melting Point: 92-96 °C(lit.)
• Optical Rotation: [α]20/D -65°, c = 1% in chloroform

Safety Information

• Storage Warning: Harmful/Irritant; IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%; 97%
• Empirical Formula (Hill Notation): C11H19NO5

DETAILS

Sigma Aldrich - 639737

Packaging
5 g in glass bottle

Toronto Research Chemicals - H656560

(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic Acid 1-tert-Butyl Ester 2-Methyl Ester is used in the synthesis of For-Met-Leu-Phe-OMe (fMLF-OMe) analogues based on Met residue replacement by 4-amino-proline scaffold.

REFERENCES

• Freer, R., et al.: Biochemistry, 21, 257 (1982)
• Higgins, J., et al.: J. Med. Chem., 39, 1013 (1982)
• Cavicchioni, G., et al.; Bioorg. Chem., 34, 298 (1982)
• Selvatici, R., et al.: Eur. J. Pharmacol., 534, 1 (1982)