{(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

Base Information

• Chemical Name: {(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
• CAS No.: 135697-39-1
• Molecular Formula: C₂₈H₄₁N₅O₆
• Molecular Weight: 543.663

Synonyms:{(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

Chemical Property of {(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of {(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

There total 12 articles about {(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 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)-1-[4-(4-tert-Butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-ylmethyl]-3-[(2-hydroxy-ethyl)-methyl-carbamoyl]-propyl}-carbamic acid tert-butyl ester (135697-39-1)

Guidance literature:

Multi-step reaction with 9 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

9: Et₃N / dimethylformamide / 2 h / 25 °C

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:

(2-hydroxyethyl)(methyl)amine (109-83-1) + (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) → {(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 (135697-39-1)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 25 ℃; for 2h;

DOI:10.1021/jo00021a010

Reference yield:

(S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester (51693-17-5) → {(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 (135697-39-1)

Guidance literature:

Multi-step reaction with 8 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

8: Et₃N / dimethylformamide / 2 h / 25 °C

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

upstream raw materials:

(2-hydroxyethyl)(methyl)amine

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

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

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

Downstream raw materials:

(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

4-tert-Butyl-benzoic acid 2-({(S)-4-{(S)-4-tert-butoxycarbonylamino-5-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-pentanoylamino}-5-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-pentanoyl}-methyl-amino)-ethyl ester

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