(S)-4-tert-Butoxycarbonylamino-5-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-pentanoic acid 4-nitro-phenyl ester

Base Information

• Chemical Name: (S)-4-tert-Butoxycarbonylamino-5-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-pentanoic acid 4-nitro-phenyl ester
• CAS No.: 135697-33-5
• Molecular Formula: C₃₁H₃₇N₅O₈
• Molecular Weight: 607.663
• Mol file: 135697-33-5.mol

Synonyms:(S)-4-tert-Butoxycarbonylamino-5-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-pentanoic acid 4-nitro-phenyl ester

Chemical Property of (S)-4-tert-Butoxycarbonylamino-5-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-pentanoic acid 4-nitro-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-tert-Butoxycarbonylamino-5-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-pentanoic acid 4-nitro-phenyl ester

There total 10 articles about (S)-4-tert-Butoxycarbonylamino-5-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-pentanoic acid 4-nitro-phenyl 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:

(S)-Pyroglutaminol (17342-08-4) → (S)-4-tert-Butoxycarbonylamino-5-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-pentanoic acid 4-nitro-phenyl ester (135697-33-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / N-methylimidazole / CH₂Cl₂ / 24 h / 0 °C

2: 62 percent / potassium tert-butoxide / dimethylsulfoxide / 18 h / 25 °C

3: dimethylformamide / 8 h / 40 °C

4: 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂

5: 79 percent / (p-toluenesulfonyl)hydrazine / CH₂Cl₂ / 24 h / 25 °C

6: 83 percent / pyridine / 8 h / Ambient temperature

7: 73 percent / 1 M LiOH / tetrahydrofuran; 2-methyl-propan-2-ol; ethanol; H₂O / 0.13 h

8: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide methiodide, 4-(dimethylamino)pyridine / CH₂Cl₂

With pyridine; 1-methyl-1H-imidazole; dmap; lithium hydroxide; potassium tert-butylate; 3-{[(ethylimino)methylene]-amino}-N,N,N-trimethyl-1-propanaminium iodide; triethylamine; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jo00021a010

Reference yield:

(S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester (51693-17-5) → (S)-4-tert-Butoxycarbonylamino-5-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-pentanoic acid 4-nitro-phenyl ester (135697-33-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 62 percent / potassium tert-butoxide / dimethylsulfoxide / 18 h / 25 °C

2: dimethylformamide / 8 h / 40 °C

3: 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂

4: 79 percent / (p-toluenesulfonyl)hydrazine / CH₂Cl₂ / 24 h / 25 °C

5: 83 percent / pyridine / 8 h / Ambient temperature

6: 73 percent / 1 M LiOH / tetrahydrofuran; 2-methyl-propan-2-ol; ethanol; H₂O / 0.13 h

7: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide methiodide, 4-(dimethylamino)pyridine / CH₂Cl₂

With pyridine; dmap; lithium hydroxide; potassium tert-butylate; 3-{[(ethylimino)methylene]-amino}-N,N,N-trimethyl-1-propanaminium iodide; triethylamine; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jo00021a010

Reference yield:

(S)-(1-tert-butoxycarbonyl-5-oxopyrrolidin-2-yl)-methyl-4-methylbenzenesulfonate (135697-21-1) → (S)-4-tert-Butoxycarbonylamino-5-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-pentanoic acid 4-nitro-phenyl ester (135697-33-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 62 percent / potassium tert-butoxide / dimethylsulfoxide / 24 h / Ambient temperature

2: 83 percent / pyridine / 8 h / Ambient temperature

3: 73 percent / 1 M LiOH / tetrahydrofuran; 2-methyl-propan-2-ol; ethanol; H₂O / 0.13 h

4: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide methiodide, 4-(dimethylamino)pyridine / CH₂Cl₂

With pyridine; dmap; lithium hydroxide; potassium tert-butylate; 3-{[(ethylimino)methylene]-amino}-N,N,N-trimethyl-1-propanaminium iodide; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol;

DOI:10.1021/jo00021a010

upstream raw materials:

(S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester

(S)-4-amino-1-<(5-oxo-2-pyrrolidinyl)methyl>-2(1H)-pyrimidinone

4-(1,1-Dimethylethyl)-N-[1,2-dihydro-2-oxo-4-pyrimidinyl]benzamide

(S)-1,1-dimethylethyl 2-<(4-amino-1,2-dihydro-2-oxo-1-pyrimidinyl)methyl>-5-oxo-1-pyrrolidinecarboxylate

Downstream raw materials:

{(S)-1-[4-(4-tert-Butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-ylmethyl]-3-[(2-hydroxy-ethyl)-methyl-carbamoyl]-propyl}-carbamic acid tert-butyl ester

C₇₀H₉₂N₁₄O₁₁

(S)-2-<<4-<<(1,1-dimethylethoxy)carbonyl>amino>-5-<4-<<4-(1,1-dimethylethyl)benzoyl>amino>-1,2-dihydro-2-oxo-1-pyrimidinyl>-1-oxopentyl>methylamino>ethyl 4-(1,2-dimethylethyl)benzoate

{(S)-1-[4-(4-tert-Butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-ylmethyl]-3-[(S)-1-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-ylmethyl]-3-(piperidin-1-ylcarbamoyl)-propylcarbamoyl]-propyl}-carbamic acid tert-butyl ester