3(R)-<(carbobenzyloxy)amino>-5-(carbomethoxymethyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Base Information

• Chemical Name: 3(R)-<(carbobenzyloxy)amino>-5-(carbomethoxymethyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one
• CAS No.: 94590-56-4
• Molecular Formula: C₂₀H₂₀N₂O₅S
• Molecular Weight: 400.455

Synonyms:3(R)-<(carbobenzyloxy)amino>-5-(carbomethoxymethyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Chemical Property of 3(R)-<(carbobenzyloxy)amino>-5-(carbomethoxymethyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Chemical Property:

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Technology Process of 3(R)-<(carbobenzyloxy)amino>-5-(carbomethoxymethyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

There total 7 articles about 3(R)-<(carbobenzyloxy)amino>-5-(carbomethoxymethyl)-2,3-dihydro-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: 70.0%

bromoacetic acid methyl ester (96-32-2) + 3(R)-<(carbobenzyloxy)amino>-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (94590-55-3) → 3(R)-<(carbobenzyloxy)amino>-5-(carbomethoxymethyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (94590-56-4)

Guidance literature:

With potassium hydroxide; tetrabutylammomium bromide; In tetrahydrofuran; for 3h; Ambient temperature;

DOI:10.1021/jm00148a024

Reference yield:

S-(o-nitrophenyl)-L-cysteine (60115-45-9) → 3(R)-<(carbobenzyloxy)amino>-5-(carbomethoxymethyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (94590-56-4)

Guidance literature:

Multi-step reaction with 4 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: 70 percent / n-Bu₄NBr, KOH / tetrahydrofuran / 3 h / Ambient temperature

With potassium hydroxide; sodium hydroxide; tetrabutylammomium bromide; ammonium chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00148a024

Reference yield:

N-acetyl-S-(2-nitro-phenyl)-L-cysteine (91088-54-9) → 3(R)-<(carbobenzyloxy)amino>-5-(carbomethoxymethyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (94590-56-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / 18 M aq. H₂SO₄ / H₂O / 0.5 h / Heating

2: 81 percent / aq. NaOH / Ambient temperature

3: 82 percent / NH₄Cl, Zn / methanol / 1.) reflux, 4 h, 2.) RT, overnight

4: 84 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 3 h

5: 70 percent / n-Bu₄NBr, KOH / tetrahydrofuran / 3 h / Ambient temperature

With potassium hydroxide; sodium hydroxide; sulfuric acid; tetrabutylammomium bromide; ammonium chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00148a024

upstream raw materials:

bromoacetic acid methyl ester

3(R)-<(carbobenzyloxy)amino>-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

S-(o-nitrophenyl)-L-cysteine

N-acetyl-S-(2-nitro-phenyl)-L-cysteine

Downstream raw materials:

((R)-3-Benzyloxycarbonylamino-1,1,4-trioxo-1,2,3,4-tetrahydro-1λ⁶-benzo[b][1,4]thiazepin-5-yl)-acetic acid methyl ester

3(R)--5-(carboxymethyl)-2,3-dihydro-1,1-dioxo-1,5-benzothiazepin-4(5H)-one hydrochloride

2-((R)-5-Methoxycarbonylmethyl-1,1,4-trioxo-2,3,4,5-tetrahydro-1H-1λ⁶-benzo[b][1,4]thiazepin-3-ylamino)-4-phenyl-butyric acid ethyl ester

2-[(Z)-(R)-5-Methoxycarbonylmethyl-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-ylimino]-4-phenyl-butyric acid ethyl ester

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