(S)-tert-Butyl 2-(3-amino-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)acetate

Base Information

• Chemical Name: (S)-tert-Butyl 2-(3-amino-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)acetate
• CAS No.: 109010-60-8
• Molecular Formula: C16H22N2O3
• Molecular Weight: 290.362
• Hs Code.: 2933790002
• European Community (EC) Number: 600-892-7,700-294-7
• UNII: 5WJ869A7AY
• DSSTox Substance ID: DTXSID80148797
• Nikkaji Number: J911.051H
• Wikidata: Q27262960
• Mol file: 109010-60-8.mol

Synonyms:109010-60-8;(S)-tert-Butyl 2-(3-amino-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)acetate;(S)-t-Butyl 2-(3-amino-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)acetate;UNII-5WJ869A7AY;1,1-Dimethylethyl ((3S)-3-amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)acetate;5WJ869A7AY;S-ATBA;tert-butyl 2-[(3S)-3-amino-2-oxo-4,5-dihydro-3H-1-benzazepin-1-yl]acetate;EC 700-294-7;(S)-3-Amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benazepine-1-acetic acid 1,1-dimethyl ethyl ester;tert-Butyl (S)-2-(3-Amino-2-oxo-2,3,4,5-tetrahydrobenzo[b]azepin-1-yl)acetate;1,1-Dimethylethyl [(3S)-3-Amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]acetate;tert-butyl 2-[(3S)-3-amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]acetate;1H-1-Benzazepine-1-acetic acid, 3-amino-2,3,4,5-tetrahydro-2-oxo-, 1,1-dimethylethyl ester, (3S)-;MFCD03426719;tert-Butyl-(S)-(3-amino-2-oxo-2,3,4,5-tetrahydrobenzo[b]azepin-1-yl) Acetate;Tert-butyl-3-amino-2,3,4,5-tetrahydro-2-oxo-1H-(3S)-benzazepine-1-acetate;Benazepril EP Impurity F;AN-668/40768843;SCHEMBL5698825;DTXSID80148797;QTEDVVHLTMELTB-LBPRGKRZSA-N;BCP13482;CS-D0726;AC-767;T-butyl,3S-amino-2,3,4,5-tetrahydro-1H-[1]benaepin-2-one-1acetate;AKOS015854177;AKOS015888693;CS-O-14883;DS-1653;A801954;J-502511;Q27262960;BENAZEPRIL HYDROCHLORIDE IMPURITY F [EP IMPURITY];tBu-(S)-(3-amino-2-oxo-2,3,4,5-tetrahydrobenzo[b]azepin-1-yl) Acetate;(3S)-2,3,4,5-Tetrahydro-2-oxo-3-amino-1H-1-benzazepine-1-acetic acid tert-butyl ester;(3S)-3-amino-1-t-butoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-benzazepin-2-one;(S)-1,1-DIMETHYLETHYL 3-AMINO-2-OXO-2,3,4,5-TETRAHYDRO-1H-BENZ(B)AZEPIN-1-ACETATE;(s)-3-amino-2,3,4,5-tetrahydro-2-oxo-1h-1-benzazepine-1-acetic acid t-butyl ester;(S)-neopentyl 2-(3-amino-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)acetate;(S)-tert-Butyl2-(3-amino-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)acetate;2-Methyl-2-propanyl [(3S)-3-amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]acetate;T-BUTYL 3-(S)-AMINO-2,3,4,5-TETRAHYDRO-1H-[1]BENZEPINE-2-ONE-1-ACETATE;tert-butyl (3-amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)acetate;tert-Butyl (3S)-3-amino-2,3,4,5-tetrahydro-1H-(1)-benzazepin-2-one-1-acetate;tert-butyl (3S)-3-amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetate;tert-butyl (3S)-3-amino-2,3,4,5-tetrahydro-2-oxo-1H-benzazepine-1-acetate;Tert-butyl-(s)-(3-amino-2-oxo-2,3,4,5-tetrahydro benzo[b]azepin-1-yl)acetate;tertButyl (3S)-3-amino-2,3,4,5-tetrahydro-1H-(1)-benzazepin-2-one-1-acetate;(S)-1-((TERT-BUTYLOXYCARBONYL)METHYL)-3-AMINO-2,3,4,5-TETRAHYDRO-1H-(1)BENZAZEPIN-2-ONE;1H-1-BENZAZEPINE-1-ACETIC ACID, 3-AMINO-2,3,4,5-TETRAHYDRO-2-OXO-, 1,1-DIMETHYLETHYL ESTER, (S)-;S-ATBA pound>>(S)-3-Amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benazepine-1-acetic acid 1,1-dimethyl ethyl ester;tert-Butyl-3-amino-2,3,4,5-tetrahydro-2-oxo-1H-(3S)-benzazepine-1-ace

Chemical Property of (S)-tert-Butyl 2-(3-amino-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)acetate

Chemical Property:

• Appearance/Colour: off-white solid
• Melting Point: 115-116 ºC
• Refractive Index: 1.543
• Boiling Point: 483.2 ºC at 760 mmHg
• PKA: 7.37±0.20(Predicted)
• Flash Point: 246 ºC
• PSA: 72.63000
• Density: 1.133 g/cm³
• LogP: 2.40010
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO: ~34 mg/mL, soluble
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 290.16304257
• Heavy Atom Count: 21
• Complexity: 403

Purity/Quality:

99% ^*data from raw suppliers

tert-Butyl-(S)-(3-amino-2-oxo-2,3,4,5-tetrahydrobenzo[b]azepin-1-yl)Acetate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CN1C2=CC=CC=C2CCC(C1=O)N
• Isomeric SMILES: CC(C)(C)OC(=O)CN1C2=CC=CC=C2CC[C@@H](C1=O)N
• Uses: S-ATBA is an intermediate in the synthesis of benazepril.

Technology Process of (S)-tert-Butyl 2-(3-amino-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)acetate

There total 10 articles about (S)-tert-Butyl 2-(3-amino-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)acetate 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: 98.0%

(S)-1-t-butyloxycarbonylmethyl-3-amino-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one tartrate salt (182561-27-9) → tert-butyl (3S)-3-amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetate (109010-60-8)

Guidance literature:

With ammonium hydroxide; In dichloromethane; water; at 0 ℃;

DOI:10.1002/hlca.19880710205

Reference yield: 93.2%

tert-butyl 2,3-dioxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetate → tert-butyl (3S)-3-amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetate (109010-60-8)

Guidance literature:

With quinine; 2-CHLOROBENZYLAMINE; In dichloromethane; at 0 - 10 ℃; for 10h; Temperature; Solvent;

Reference yield:

3-bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (86499-96-9) → tert-butyl (3S)-3-amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetate (109010-60-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / Na₂CO₃, propylene glycol / 3.5 h / 130 °C

2: 88 percent / odorless mineral spirits / 16 h / 140 °C

3: 1.) tetrabutylammonium hydrogen sulfate, 50percent NaOH, 3.) H₂ / 3.) 5percent Pd/C / 1.) toluene, 35 deg C, 1 h; 20 deg C, 16 h, 2.) toluene, 20 deg C, 1 h, 3.) EtOH, 60 deg C, 55 psi, 16 h

With sodium hydroxide; propylene glycol; odorless mineral spirits; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; palladium on activated charcoal;

DOI:10.1021/jo971056n

upstream raw materials:

(S)-1-t-butyloxycarbonylmethyl-3-amino-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one tartrate salt

tert-Butyl chloroacetate

(S)-3-((S)-1-Phenyl-ethylamino)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

3-bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Downstream raw materials:

[S-(R*,R*)]-2,3,4,5-tetrahydro-3-[[2-[[(4-methoxyphenyl)methyl]thio]-2-methyl-1-oxo-3-phenylpropyl]amino]-2-oxo-1H-benzazepine-1-acetic acid, 1,1,-dimethylethyl ester

(2S,3'S)-2-(1-tert-butoxycarbonylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenylbutyric acid ethyl ester

Refernces

• 1、 -. "PROCESS FOR PREPARATION OF BENAZEPRIL". Page/Page column 16. . Retrieved 2008/06/13.
• 2、 -. "Pharmaceuticals which promote gastrointestinal blood circulation". . . Retrieved 2008/06/13.