(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1,5-benzothiazepin-4-one

• ChemBase ID: 150136
• Molecular Formular: C16H15NO3S
• Molecular Mass: 301.3602
• Monoisotopic Mass: 301.07726435
• SMILES: COc1ccc(cc1)[C@H]1[C@H](C(=O)Nc2ccccc2S1)O
• Canonical SMILES: COc1ccc(cc1)[C@@H]1Sc2ccccc2NC(=O)[C@@H]1O
• InChI: InChI=1S/C16H15NO3S/c1-20-11-8-6-10(7-9-11)15-14(18)16(19)17-12-4-2-3-5-13(12)21-15/h2-9,14-15,18H,1H3,(H,17,19)/t14-,15+/m1/s1
• InChIKey: LHBHZALHFIQJGJ-CABCVRRESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1,5-benzothiazepin-4-one
• IUPAC Traditional name: (2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-3,5-dihydro-2H-1,5-benzothiazepin-4-one
• Synonyms: (2S,3S)-2,3-Dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one; (2S-cis)-2,3-Dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one; Des[3-Acetyl-5-(2-dimethylamino)ethyl] Diltiazem; (2S-cis)-(+)-2,3-Dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one; (2S-cis)-(+)-2,3-二氢-3-羟基-2-(4-甲氧苯基)-1,5-苯并硫氮杂卓-4(5H)-酮

Database IDs

• CAS Number: 42399-49-5
• EC Number: 255-799-0
• MDL Number: MFCD01321316
• PubChem SID: 162244298; 24871144
• PubChem CID: 2733673

CALCULATED PROPERTIES

• Acid pKa: 11.85173
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.4034157
• LogD (pH = 7.4): 2.4034011
• Log P: 2.403416
• Molar Refractivity: 84.0798 cm^3
• Polarizability: 32.097275 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 202-203°C; 203-206 °C(lit.)
• Optical Rotation: [α]20/D +112°, c = 0.5 in methanol

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C16H15NO3S

DETAILS

Sigma Aldrich - 475548

Packaging
5 g in glass bottle

Toronto Research Chemicals - D288450

A key intermediate for Diltiazem (D460620) synthesis.

REFERENCES

• Nagao, T., et al.: Jpn. J. Pharmacol., 22, 1 (1972)
• Senuma, M., et al.: Chem. Pharm. Bull., 37, 3204 (1972)
• Kometani, T., et al.: J. Ferment. Bioeng., 80, 208 (1972)