(S)-γ-<<(1,1-dimethylethoxy)carbonyl>amino>-4-(benzoylamino)-1,2-dihydro-2-oxo-1-pyrimidinepentanoic acid

Base Information

Chemical Name:(S)-γ-<<(1,1-dimethylethoxy)carbonyl>amino>-4-(benzoylamino)-1,2-dihydro-2-oxo-1-pyrimidinepentanoic acid
CAS No.:135697-20-0
Molecular Formula:C₂₁H₂₆N₄O₆
Molecular Weight:430.461
Hs Code.:

Synonyms:(S)-γ-<<(1,1-dimethylethoxy)carbonyl>amino>-4-(benzoylamino)-1,2-dihydro-2-oxo-1-pyrimidinepentanoic acid

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

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

There total 9 articles about (S)-γ-<<(1,1-dimethylethoxy)carbonyl>amino>-4-(benzoylamino)-1,2-dihydro-2-oxo-1-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: 70.0%

: 135697-18-6
(S)-1,1-dimethylethyl 2-<<4-(benzoylamino)-1,2-dihydro-2-oxo-1-pyrimidinyl>methyl>-5-oxo-1-pyrrolidinecarboxylate

: 135697-20-0
(S)-γ-<<(1,1-dimethylethoxy)carbonyl>amino>-4-(benzoylamino)-1,2-dihydro-2-oxo-1-pyrimidinepentanoic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; 1) 0 deg C, 15 min, 2) 25 deg C, 30 min;
DOI:10.1021/jo00021a010

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 135697-20-0
(S)-γ-<<(1,1-dimethylethoxy)carbonyl>amino>-4-(benzoylamino)-1,2-dihydro-2-oxo-1-pyrimidinepentanoic acid

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: 70 percent / pyridine / 8 h / Ambient temperature

7: 70 percent / 1 M LiOH / tetrahydrofuran / 1) 0 deg C, 15 min, 2) 25 deg C, 30 min

With pyridine; 1-methyl-1H-imidazole; dmap; lithium hydroxide; potassium tert-butylate; triethylamine; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo00021a010

Reference yield:

: 51693-17-5
(S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester

: 135697-20-0
(S)-γ-<<(1,1-dimethylethoxy)carbonyl>amino>-4-(benzoylamino)-1,2-dihydro-2-oxo-1-pyrimidinepentanoic acid

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: 70 percent / pyridine / 8 h / Ambient temperature

6: 70 percent / 1 M LiOH / tetrahydrofuran / 1) 0 deg C, 15 min, 2) 25 deg C, 30 min

With pyridine; dmap; lithium hydroxide; potassium tert-butylate; triethylamine; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo00021a010