3(R)-[N-(1(S)-carboxy-3-phenylpropyl)amino]-5-(carboxymethyl)-2,3-dihydro-1-oxo-1,5-benzothiazepin-4(5H)-one

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Chemical Name:3(R)-[N-(1(S)-carboxy-3-phenylpropyl)amino]-5-(carboxymethyl)-2,3-dihydro-1-oxo-1,5-benzothiazepin-4(5H)-one
CAS No.:94590-34-8
Molecular Formula:C₂₁H₂₂N₂O₆S
Molecular Weight:430.481
Hs Code.:

Synonyms:3(R)-[N-(1(S)-carboxy-3-phenylpropyl)amino]-5-(carboxymethyl)-2,3-dihydro-1-oxo-1,5-benzothiazepin-4(5H)-one

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Chemical Property of 3(R)-[N-(1(S)-carboxy-3-phenylpropyl)amino]-5-(carboxymethyl)-2,3-dihydro-1-oxo-1,5-benzothiazepin-4(5H)-one

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Technology Process of 3(R)-[N-(1(S)-carboxy-3-phenylpropyl)amino]-5-(carboxymethyl)-2,3-dihydro-1-oxo-1,5-benzothiazepin-4(5H)-one

There total 12 articles about 3(R)-[N-(1(S)-carboxy-3-phenylpropyl)amino]-5-(carboxymethyl)-2,3-dihydro-1-oxo-1,5-benzothiazepin-4(5H)-one 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: 44.0%

: 94590-33-7
(S)-2-((R)-5-Methoxycarbonylmethyl-1,4-dioxo-2,3,4,5-tetrahydro-1H-1λ⁴-benzo[b][1,4]thiazepin-3-ylamino)-4-phenyl-butyric acid ethyl ester

: 94590-34-8
3(R)-[N-(1(S)-carboxy-3-phenylpropyl)amino]-5-(carboxymethyl)-2,3-dihydro-1-oxo-1,5-benzothiazepin-4(5H)-one

Guidance literature:: With sodium hydroxide; In methanol;
DOI:10.1021/jm00148a024

Reference yield:

: 60115-45-9
S-(o-nitrophenyl)-L-cysteine

: 94590-34-8
3(R)-[N-(1(S)-carboxy-3-phenylpropyl)amino]-5-(carboxymethyl)-2,3-dihydro-1-oxo-1,5-benzothiazepin-4(5H)-one

Guidance literature:: Multi-step reaction with 9 steps

1: 81 percent / aq. NaOH / Ambient temperature

2: 82 percent / NH₄Cl, Zn / methanol / 1.) reflux, 4 h, 2.) RT, overnight

3: 84 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 3 h

4: 68 percent / 31percent HBr in HOAc / 1 h / Ambient temperature

5: 25.4 g / BF₃*Et₂O / CHCl₃ / 18 h / Ambient temperature

6: sodium cyanoborohydride, glacial acetic acid / ethanol

7: 48 percent / n-Bu₄NBr, KOH / tetrahydrofuran / 3 h / Ambient temperature

8: sodium periodate / methanol; H₂O / 72 h / Ambient temperature

9: 44 percent / 1N aq. NaOH / methanol

With potassium hydroxide; sodium hydroxide; sodium periodate; boron trifluoride diethyl etherate; tetrabutylammomium bromide; hydrogen bromide; sodium cyanoborohydride; ammonium chloride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; In tetrahydrofuran; methanol; ethanol; chloroform; water; N,N-dimethyl-formamide;
DOI:10.1021/jm00148a024

Reference yield:

: 64920-29-2
2-oxo-4-phenylbutanoic acid ethyl ester

: 94590-34-8
3(R)-[N-(1(S)-carboxy-3-phenylpropyl)amino]-5-(carboxymethyl)-2,3-dihydro-1-oxo-1,5-benzothiazepin-4(5H)-one

Guidance literature:: Multi-step reaction with 5 steps

1: 25.4 g / BF₃*Et₂O / CHCl₃ / 18 h / Ambient temperature

2: sodium cyanoborohydride, glacial acetic acid / ethanol

3: 48 percent / n-Bu₄NBr, KOH / tetrahydrofuran / 3 h / Ambient temperature

4: sodium periodate / methanol; H₂O / 72 h / Ambient temperature

5: 44 percent / 1N aq. NaOH / methanol

With potassium hydroxide; sodium hydroxide; sodium periodate; boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium cyanoborohydride; acetic acid; In tetrahydrofuran; methanol; ethanol; chloroform; water;
DOI:10.1021/jm00148a024