(S)-N-{(S)-1-[((1S,2R)-1-((S)-sec-Butyl)-2-methoxy-4-{(S)-2-[(1R,2S)-1-methoxy-2-((S)-2-phenyl-1-thiazol-2-yl-ethylcarbamoyl)-propyl]-pyrrolidin-1-yl}-4-oxo-butyl)-methyl-carbamoyl]-2-methyl-propyl}-2-dimethylamino-3-methyl-butyramide

Base Information

• Chemical Name: (S)-N-{(S)-1-[((1S,2R)-1-((S)-sec-Butyl)-2-methoxy-4-{(S)-2-[(1R,2S)-1-methoxy-2-((S)-2-phenyl-1-thiazol-2-yl-ethylcarbamoyl)-propyl]-pyrrolidin-1-yl}-4-oxo-butyl)-methyl-carbamoyl]-2-methyl-propyl}-2-dimethylamino-3-methyl-butyramide
• CAS No.: 130272-92-3
• Molecular Formula: C₄₂H₆₈N₆O₆S
• Molecular Weight: 785.105
• Mol file: 130272-92-3.mol

Synonyms:

Chemical Property of (S)-N-{(S)-1-[((1S,2R)-1-((S)-sec-Butyl)-2-methoxy-4-{(S)-2-[(1R,2S)-1-methoxy-2-((S)-2-phenyl-1-thiazol-2-yl-ethylcarbamoyl)-propyl]-pyrrolidin-1-yl}-4-oxo-butyl)-methyl-carbamoyl]-2-methyl-propyl}-2-dimethylamino-3-methyl-butyramide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-{(S)-1-[((1S,2R)-1-((S)-sec-Butyl)-2-methoxy-4-{(S)-2-[(1R,2S)-1-methoxy-2-((S)-2-phenyl-1-thiazol-2-yl-ethylcarbamoyl)-propyl]-pyrrolidin-1-yl}-4-oxo-butyl)-methyl-carbamoyl]-2-methyl-propyl}-2-dimethylamino-3-methyl-butyramide

There total 12 articles about (S)-N-{(S)-1-[((1S,2R)-1-((S)-sec-Butyl)-2-methoxy-4-{(S)-2-[(1R,2S)-1-methoxy-2-((S)-2-phenyl-1-thiazol-2-yl-ethylcarbamoyl)-propyl]-pyrrolidin-1-yl}-4-oxo-butyl)-methyl-carbamoyl]-2-methyl-propyl}-2-dimethylamino-3-methyl-butyramide 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:

Boc-L-Pro-H (69610-41-9,117625-90-8) → (S)-N-{(S)-1-[((1S,2R)-1-((S)-sec-Butyl)-2-methoxy-4-{(S)-2-[(1R,2S)-1-methoxy-2-((S)-2-phenyl-1-thiazol-2-yl-ethylcarbamoyl)-propyl]-pyrrolidin-1-yl}-4-oxo-butyl)-methyl-carbamoyl]-2-methyl-propyl}-2-dimethylamino-3-methyl-butyramide (130272-92-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 11 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

2: 34 percent / BF₃*OEt₂ / CH₂Cl₂

3: H₂ / 5percent Pd/C / 2-methyl-propan-2-ol; H₂O / 2 h

4: benzotriazolyloxytris(dimethylamino)phosphonium hexafluorophosphate, iso-Pr₂NEt / acetonitrile / 4 h / Ambient temperature

5: HCl / dioxane

6: diethyl phosphorocyanidate, Et₃N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h

With hydrogenchloride; diethyl cyanophosphonate; boron trifluoride diethyl etherate; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1248/cpb.43.1706

Reference yield:

benzyl (2S,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate (173653-47-9) → (S)-N-{(S)-1-[((1S,2R)-1-((S)-sec-Butyl)-2-methoxy-4-{(S)-2-[(1R,2S)-1-methoxy-2-((S)-2-phenyl-1-thiazol-2-yl-ethylcarbamoyl)-propyl]-pyrrolidin-1-yl}-4-oxo-butyl)-methyl-carbamoyl]-2-methyl-propyl}-2-dimethylamino-3-methyl-butyramide (130272-92-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 34 percent / BF₃*OEt₂ / CH₂Cl₂

2: H₂ / 5percent Pd/C / 2-methyl-propan-2-ol; H₂O / 2 h

3: benzotriazolyloxytris(dimethylamino)phosphonium hexafluorophosphate, iso-Pr₂NEt / acetonitrile / 4 h / Ambient temperature

4: HCl / dioxane

5: diethyl phosphorocyanidate, Et₃N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h

With hydrogenchloride; diethyl cyanophosphonate; boron trifluoride diethyl etherate; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1248/cpb.43.1706

Reference yield:

(3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid (135383-56-1) → (S)-N-{(S)-1-[((1S,2R)-1-((S)-sec-Butyl)-2-methoxy-4-{(S)-2-[(1R,2S)-1-methoxy-2-((S)-2-phenyl-1-thiazol-2-yl-ethylcarbamoyl)-propyl]-pyrrolidin-1-yl}-4-oxo-butyl)-methyl-carbamoyl]-2-methyl-propyl}-2-dimethylamino-3-methyl-butyramide (130272-92-3)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂SO₄ / CH₂Cl₂

2: H₂ / 5percent Pd/C / 2-methyl-propan-2-ol; H₂O / 2 h

3: 1,3-dicyclohexylcarbodiimide / CH₂Cl₂

4: H₂ / 5percent Pd/C / 2-methyl-propan-2-ol; H₂O / 2 h

5: diethyl phosphorocyanidate, Et₃N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h

6: trifluoroacetic acid / CH₂Cl₂ / 1 h / Ambient temperature

7: diethyl phosphorocyanidate, Et₃N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h

With diethyl cyanophosphonate; sulfuric acid; hydrogen; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1248/cpb.43.1706

upstream raw materials:

(3R,4S,5S)-4-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoic acid

Boc-L-Pro-H

(3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid

tert-Butyl (3R,4S,5S)-3-methoxy-4--5-methylheptanoate