(S)-γ-<<(1,1-dimethylethoxy)carbonyl>amino>-4-<<4-(1,1-dimethylethyl)benzoyl>amino>-2-oxo-1(2H)-pyrimidinepentanoic acid

Base Information

• Chemical Name: (S)-γ-<<(1,1-dimethylethoxy)carbonyl>amino>-4-<<4-(1,1-dimethylethyl)benzoyl>amino>-2-oxo-1(2H)-pyrimidinepentanoic acid
• CAS No.: 135697-26-6
• Molecular Formula: C₂₅H₃₄N₄O₆
• Molecular Weight: 486.568

Synonyms:(S)-γ-<<(1,1-dimethylethoxy)carbonyl>amino>-4-<<4-(1,1-dimethylethyl)benzoyl>amino>-2-oxo-1(2H)-pyrimidinepentanoic acid

Chemical Property of (S)-γ-<<(1,1-dimethylethoxy)carbonyl>amino>-4-<<4-(1,1-dimethylethyl)benzoyl>amino>-2-oxo-1(2H)-pyrimidinepentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (S)-γ-<<(1,1-dimethylethoxy)carbonyl>amino>-4-<<4-(1,1-dimethylethyl)benzoyl>amino>-2-oxo-1(2H)-pyrimidinepentanoic acid

There total 10 articles about (S)-γ-<<(1,1-dimethylethoxy)carbonyl>amino>-4-<<4-(1,1-dimethylethyl)benzoyl>amino>-2-oxo-1(2H)-pyrimidinepentanoic acid 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: 73.0%

(S)-1,1-dimethylethyl 2-<<4-<<4-(1,1-dimethylethyl)benzoyl>amino>-1,2-dihydro-2-oxo-1-pyrimidinyl>methyl>-5-oxo-1-pyrrolidinecarboxylate (135697-24-4) → (S)-γ-<<(1,1-dimethylethoxy)carbonyl>amino>-4-<<4-(1,1-dimethylethyl)benzoyl>amino>-2-oxo-1(2H)-pyrimidinepentanoic acid (135697-26-6)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; ethanol; water; tert-butyl alcohol; for 0.133333h;

DOI:10.1021/jo00021a010

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → (S)-γ-<<(1,1-dimethylethoxy)carbonyl>amino>-4-<<4-(1,1-dimethylethyl)benzoyl>amino>-2-oxo-1(2H)-pyrimidinepentanoic acid (135697-26-6)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; 1-methyl-1H-imidazole; dmap; lithium hydroxide; potassium tert-butylate; 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)-γ-<<(1,1-dimethylethoxy)carbonyl>amino>-4-<<4-(1,1-dimethylethyl)benzoyl>amino>-2-oxo-1(2H)-pyrimidinepentanoic acid (135697-26-6)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; dmap; lithium hydroxide; potassium tert-butylate; triethylamine; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jo00021a010

upstream raw materials:

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

(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

Downstream raw materials:

C₇₀H₉₂N₁₄O₁₁

{(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

(S)-1,1-dimethylethyl <1-<<4-<<4-(1,1-dimethylethyl)benzoyl>amino>-1,2-dihydro-2-oxo-1-pyrimidinyl>methyl>-4-oxo-4-(1-piperidinylamino)butyl>carbamate

(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

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