1-tert-butyl 2-methyl (2S,4R)-4-[(4-methylbenzenesulfonyl)oxy]pyrrolidine-1,2-dicarboxylate

• ChemBase ID: 143235
• Molecular Formular: C18H25NO7S
• Molecular Mass: 399.4586
• Monoisotopic Mass: 399.13517315
• SMILES: Cc1ccc(cc1)S(=O)(=O)O[C@@H]1C[C@H](N(C1)C(=O)OC(C)(C)C)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H]1C[C@H](CN1C(=O)OC(C)(C)C)OS(=O)(=O)c1ccc(cc1)C
• InChI: InChI=1S/C18H25NO7S/c1-12-6-8-14(9-7-12)27(22,23)26-13-10-15(16(20)24-5)19(11-13)17(21)25-18(2,3)4/h6-9,13,15H,10-11H2,1-5H3/t13-,15+/m1/s1
• InChIKey: UKVKNGDXVREPDE-HIFRSBDPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-tert-butyl 2-methyl (2S,4R)-4-[(4-methylbenzenesulfonyl)oxy]pyrrolidine-1,2-dicarboxylate
• IUPAC Traditional name: 1-tert-butyl 2-methyl (2S,4R)-4-[(4-methylbenzenesulfonyl)oxy]pyrrolidine-1,2-dicarboxylate
• Synonyms: (2S,4R)-4-[[(4-Methylphenyl)sulfonyl]oxy]-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl) 2-Methyl Ester; tert-Butyl Methyl (2S,4R)-4-[[(4-Methylphenyl)sulfonyl]oxy]pyrrolidine-1,2-dicarboxylate; trans-N-tert-Butyloxycarbonyl-4-tosyloxy-L-proline Methyl Ester; (4R)-4-TsO-N-Boc-Pro-OMe; (2S,4R)-4-{[(4-Methylphenyl)sulfonyl]oxy]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl ester; N-Boc-trans-4-(p-tosyloxy)-L-proline methyl ester; (2S,4R)-4-{[(4-甲基苯基)磺酰基]氧基]-1,2-吡咯烷二羧酸 1-(1,1-二甲基乙基) 2-甲酯; N-Boc-反式-4-(对甲苯磺酰氧基)-L-脯氨酸甲酯

Database IDs

• CAS Number: 88043-21-4
• MDL Number: MFCD02179383
• Beilstein Number: 7231334
• PubChem SID: 162237456
• PubChem CID: 13425772

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.74836
• LogD (pH = 7.4): 2.74836
• Log P: 2.74836
• Molar Refractivity: 97.0891 cm^3
• Polarizability: 39.233807 Å^3
• Polar Surface Area: 99.21 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Compostion: carbon, 53.3-54.9%; nitrogen, 3.2-3.8%
• Empirical Formula (Hill Notation): C18H25NO7S

DETAILS

Sigma Aldrich - 728020

Packaging
1 g in glass bottle

Toronto Research Chemicals - B693485

4-Hydroxy-L-proline (H952376) derivative. Used in the preparation of bicycloazahydantoins, as androgen receptor antagonists

REFERENCES

• Balog, A. et al.: Bioorgan. Med. Chem. Lett. 14, 6107 (2004)