4-[(R)-3-((R)-5-tert-Butoxycarbonylmethyl-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-ylamino)-3-ethoxycarbonyl-propyl]-piperidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: 4-[(R)-3-((R)-5-tert-Butoxycarbonylmethyl-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-ylamino)-3-ethoxycarbonyl-propyl]-piperidine-1-carboxylic acid benzyl ester
• CAS No.: 100277-06-3
• Molecular Formula: C₃₄H₄₅N₃O₇S
• Molecular Weight: 639.813
• Mol file: 100277-06-3.mol

Synonyms:

Chemical Property of 4-[(R)-3-((R)-5-tert-Butoxycarbonylmethyl-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-ylamino)-3-ethoxycarbonyl-propyl]-piperidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[(R)-3-((R)-5-tert-Butoxycarbonylmethyl-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-ylamino)-3-ethoxycarbonyl-propyl]-piperidine-1-carboxylic acid benzyl ester

There total 6 articles about 4-[(R)-3-((R)-5-tert-Butoxycarbonylmethyl-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-ylamino)-3-ethoxycarbonyl-propyl]-piperidine-1-carboxylic acid benzyl ester 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: 30.0%

ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate (99198-78-4) + tert-butyl (R)-3-amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate (95779-67-2) → 4-[(R)-3-((R)-5-tert-Butoxycarbonylmethyl-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-ylamino)-3-ethoxycarbonyl-propyl]-piperidine-1-carboxylic acid benzyl ester (100277-06-3) + tert-butyl 3(R)[3-(1-benzyloxycarbonyl-4-piperidyl)-1(S)-ethoxycarbonylpropyl]-amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate (100277-07-4)

Guidance literature:

With triethylamine; potassium iodide; Heating;

DOI:10.1248/cpb.34.3747

Reference yield:

ethyl 3-(4-pyridinyl)-(2E)-propenoate (123293-78-7) → 4-[(R)-3-((R)-5-tert-Butoxycarbonylmethyl-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-ylamino)-3-ethoxycarbonyl-propyl]-piperidine-1-carboxylic acid benzyl ester (100277-06-3)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / PtO₂ / acetic acid / Ambient temperature

2: 73 percent / NaHCO₃ / H₂O; ethyl acetate / Ambient temperature

3: 87 percent / 1.) NaOEt; 2.) LiCl / 1.) ethanol, 60-70 deg C, 1h; 2.) water, DMSO, 140-150 deg C, 45 min

4: 14 percent / AcOH, molecular sieves, NaBH₃CN / ethanol / Ambient temperature

With molecular sieve; hydrogen; sodium ethanolate; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; lithium chloride; platinum(IV) oxide; In ethanol; water; acetic acid; ethyl acetate;

DOI:10.1248/cpb.34.3747

Reference yield:

ethyl 3-(piperid-4-yl)propionate (71879-55-5) → 4-[(R)-3-((R)-5-tert-Butoxycarbonylmethyl-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-ylamino)-3-ethoxycarbonyl-propyl]-piperidine-1-carboxylic acid benzyl ester (100277-06-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / NaHCO₃ / H₂O; ethyl acetate / Ambient temperature

2: 87 percent / 1.) NaOEt; 2.) LiCl / 1.) ethanol, 60-70 deg C, 1h; 2.) water, DMSO, 140-150 deg C, 45 min

3: 14 percent / AcOH, molecular sieves, NaBH₃CN / ethanol / Ambient temperature

With molecular sieve; sodium ethanolate; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; lithium chloride; In ethanol; water; ethyl acetate;

DOI:10.1248/cpb.34.3747

upstream raw materials:

ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate

tert-butyl (R)-3-amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate

ethyl 3-(piperid-4-yl)propionate

ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-oxobutyrate

Refernces