2-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(phenylMethoxy)carbonyl]aMino]butyl]-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxaMide

Base Information

• Chemical Name: 2-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(phenylMethoxy)carbonyl]aMino]butyl]-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxaMide
• CAS No.: 137431-05-1
• Molecular Formula: C₃₂H₄₅N₃O₄
• Molecular Weight: 535.727
• Mol file: 137431-05-1.mol

Synonyms:2-<3(S)-(Benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl>-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide

Chemical Property of 2-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(phenylMethoxy)carbonyl]aMino]butyl]-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxaMide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(phenylMethoxy)carbonyl]aMino]butyl]-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxaMide

There total 9 articles about 2-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(phenylMethoxy)carbonyl]aMino]butyl]-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxaMide 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: 86.0%

(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide (128019-40-9,149510-73-6,136465-81-1,168899-60-3) + (2R,2S)-(3S)-1,2-epoxy-3-phenylmethoxycarbonylamino-4-phenylbutane (198020-19-8) → 2-<3(S)-(Benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl>-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide (137431-05-1)

Guidance literature:

In isopropyl alcohol; at 80 ℃; for 6h;

DOI:10.1021/jo00092a026

Reference yield: 60.3%

N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane (128018-44-0) + (3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide (128019-40-9,149510-73-6,136465-81-1,168899-60-3) → 2-<3(S)-(Benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl>-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide (137431-05-1)

Guidance literature:

In isopropyl alcohol; for 5h; Heating;

DOI:10.1021/jm020537i

Reference yield:

N-Cbz-L-Phe (1161-13-3) → 2-<3(S)-(Benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl>-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide (137431-05-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) carbonyldiimidazole

2: NaBH₄ / ethanol / 1 h / -15 - -10 °C

3: 89 percent / TsOH*H₂O / 5 h / 60 °C

4: 92 percent / 1 M aq. NaOH / ethanol / 18 h / Ambient temperature

5: (COCl)2, DMF / toluene / 1 h

6: CBrCl₃, 2-mercaptopyridine N-oxide sodium salt, 4-(dimethylamino)pyridine / 1 h / 80 °C / Irradiation

7: aq. AcOH, conc. HCl / 3 h / Ambient temperature

8: 92 percent / KOH / methanol / 3 h / Ambient temperature

9: 86 percent / propan-2-ol / 6 h / 80 °C

With hydrogenchloride; dmap; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; Bromotrichloromethane; 2-mercaptopyridine-1-oxide sodium salt; toluene-4-sulfonic acid; acetic acid; N,N-dimethyl-formamide; 1,1'-carbonyldiimidazole; In methanol; ethanol; isopropyl alcohol; toluene;

DOI:10.1021/jo00092a026

upstream raw materials:

(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide

(2R,2S)-(3S)-1,2-epoxy-3-phenylmethoxycarbonylamino-4-phenylbutane

N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane

N-Cbz-L-Phe

Downstream raw materials:

cis-N-butyldecahydro-2-<2(R)-hydroxy-4-phenyl-3(S)-aminobutyl>-(4aS,8aS)-isoquinoline-3(S)-carboxamide

(3S,4aS,8aS)-2-{(2R,3S)-3-[(S)-2-Amino-3-(naphthalen-2-ylsulfanyl)-propionylamino]-2-hydroxy-4-phenyl-butyl}-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

(3S,4aS,8aS)-2-{(2R,3S)-2-Hydroxy-3-[(S)-2-methanesulfonylamino-3-(naphthalen-2-ylsulfanyl)-propionylamino]-4-phenyl-butyl}-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

(3S,4aS,8aS)-2-{(2R,3S)-2-Hydroxy-3-[(S)-2-methanesulfonylamino-3-(naphthalene-2-sulfinyl)-propionylamino]-4-phenyl-butyl}-decahydro-isoquinoline-3-carboxylic acid tert-butylamide