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

• ChemBase ID: 142926
• Molecular Formular: C11H19NO5
• Molecular Mass: 245.27226
• Monoisotopic Mass: 245.12632271
• SMILES: CC(C)(C)OC(=O)N1C[C@H](C[C@H]1C(=O)OC)O
• 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-/m0/s1
• InChIKey: MZMNEDXVUJLQAF-YUMQZZPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-tert-butyl 2-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate
• IUPAC Traditional name: 1-tert-butyl 2-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate
• Synonyms: N-Boc-cis-4-hydroxy-L-proline methyl ester; N-Boc-cis-4-hydroxy-L-proline methyl ester; Boc-cis-Hyp-OMe; (2S,4S)-4-Hydroxy-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl) 2-Methyl Ester; (2S-cis)-4-Hydroxy-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl) 2-Methyl Ester; Methyl (2S,4S)-1-tert-Butoxycarbonyl-4-hydroxypyrrolidine-2-carboxylate; Methyl (4S)-N-Boc-4-hydroxy-L-prolinate; (2S,4S)-4-Hydroxypyrrolidine-1,2-dicarboxylic Acid 1-tert-Butyl Ester 2-Methyl Ester; N-Boc-顺式-4-羟基-L-脯氨酸甲酯

Database IDs

• CAS Number: 102195-79-9
• MDL Number: MFCD00237541
• PubChem SID: 162237152; 24884007
• PubChem CID: 10752873

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

• Melting Point: 81-84°C; 82-86 °C(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22-36/37/38-43; 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H317-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

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

DETAILS

Sigma Aldrich - 654000

Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - H656565

2S,4S)-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)