3(S)-Boc-amino-2,3-dihydro-4-oxo-1,5-benzothiazepine

Base Information

• Chemical Name: 3(S)-Boc-amino-2,3-dihydro-4-oxo-1,5-benzothiazepine
• CAS No.: 440634-11-7
• Molecular Formula: C₁₄H₁₈N₂O₃S
• Molecular Weight: 294.375
• DSSTox Substance ID: DTXSID60458109
• Wikidata: Q82281253
• Mol file: 440634-11-7.mol

Synonyms:440634-11-7;(S)-tert-butyl (4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-yl)carbamate;TERT-BUTYL N-[(3S)-4-OXO-3,5-DIHYDRO-2H-1,5-BENZOTHIAZEPIN-3-YL]CARBAMATE;3(S)-Boc-amino-2,3-dihydro-4-oxo-1,5-benzothiazepine;DTXSID60458109;AC-30741;C15807;(S)-tert-butyl(4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-yl)carbamate;tert-Butyl [(3S)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl]carbamate

Chemical Property of 3(S)-Boc-amino-2,3-dihydro-4-oxo-1,5-benzothiazepine

Chemical Property:

• Vapor Pressure: 8.34E-10mmHg at 25°C
• Boiling Point: 491.5°C at 760 mmHg
• Flash Point: 251°C
• PSA: 92.73000
• Density: 1.26g/cm³
• LogP: 3.15300
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 294.10381361
• Heavy Atom Count: 20
• Complexity: 381

Purity/Quality:

97% ^*data from raw suppliers

(S)-tert-Butyl (4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-yl)carbamate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CSC2=CC=CC=C2NC1=O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H]1CSC2=CC=CC=C2NC1=O

Technology Process of 3(S)-Boc-amino-2,3-dihydro-4-oxo-1,5-benzothiazepine

There total 4 articles about 3(S)-Boc-amino-2,3-dihydro-4-oxo-1,5-benzothiazepine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

(S)-3-((2-aminophenyl)thio)-2-((tert-butoxycarbonyl)amino)propionic acid (440634-06-0) → (S)-3-(tert-butyloxycarbonylamino)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (440634-11-7)

Guidance literature:

With sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1080/00304940209458076

Reference yield:

ortho-nitrofluorobenzene (1493-27-2,127723-77-7) → (S)-3-(tert-butyloxycarbonylamino)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (440634-11-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / sodium hydrogen carbonate / ethanol; H₂O / 6 h / Heating

2: 100 percent / zinc; ammonium chloride / methanol / 4 h / 20 - 75 °C

3: 75 percent / benzotriazolyloxy-tris(dimethylamino)phosphonium PF₆-; sodium hydrogen carbonate / dimethylformamide / 20 °C

With ammonium chloride; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; zinc; In methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1080/00304940209458076

Reference yield:

(S)-N-(tert-butyloxycarbonyl)cysteine → (S)-3-(tert-butyloxycarbonylamino)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (440634-11-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / sodium hydrogen carbonate / ethanol; H₂O / 6 h / Heating

2: 100 percent / zinc; ammonium chloride / methanol / 4 h / 20 - 75 °C

3: 75 percent / benzotriazolyloxy-tris(dimethylamino)phosphonium PF₆-; sodium hydrogen carbonate / dimethylformamide / 20 °C

With ammonium chloride; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; zinc; In methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1080/00304940209458076

upstream raw materials:

(S)-3-((2-aminophenyl)thio)-2-((tert-butoxycarbonyl)amino)propionic acid

ortho-nitrofluorobenzene

(S)-2-((tert-butoxycarbonyl)amino)-3-((2-nitrophenyl)thio)propionic acid

Downstream raw materials:

(S)-3-(tert-butyloxycarbonylamino)-5-(carboxymethyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

(S)-3-(tert-butyloxycarbonylamino)-5-(carboethoxymethyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Refernces

• 1、 Amblard, Muriel,Calmes, Monique,Roques, Virginie,Tabet, Samuel,Loffet, Albert,Martinez, Jean. "An improved synthesis of (S)- or (R)-N-Boc-protected 1,5-benzothiazepine derivatives". . p. 405 - 415. Retrieved 2007/10/03.