(S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester
• CAS No.: 176752-38-8
• Molecular Formula: C₄₄H₅₂N₁₀O₇
• Molecular Weight: 832.96

Synonyms:(S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester

Chemical Property of (S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester

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Technology Process of (S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester

There total 10 articles about (S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl 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: 45.0%

pyrimidoblamic acid (75452-30-1) + (S)-2-Methylamino-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester (176752-37-7) → (S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester (176752-38-8)

Guidance literature:

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In dichloromethane; at 25 ℃; for 6h;

DOI:10.1016/0968-0896(95)00183-2

Reference yield:

trityl chloride (76-83-5) → (S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester (176752-38-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / Et₃N / benzene / 1 h / 80 °C

2: 0.78 g / H₂ / 10percent Pd/C / methanol / 2.5 h / 25 °C / 760 Torr

3: methanol / 1.5 h / 25 °C

4: NaBH₄ / methanol / 0.5 h / 5 - 10 °C

5: 61 percent / NaBH₃CN, aq. AcOH / acetonitrile / 0.33 h / 25 °C

6: 38 percent / H₂ / 10percent Pd/C / methanol / 10 h / 25 °C / 760 Torr

7: 45 percent / BOPCl, Et₃N / CH₂Cl₂ / 6 h / 25 °C

With sodium tetrahydroborate; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium cyanoborohydride; acetic acid; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile; benzene;

DOI:10.1016/0968-0896(95)00183-2

Reference yield:

1,Nα-bis-benzyloxycarbonyl-histidine methyl ester (40917-50-8) → (S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester (176752-38-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / 1N aq. NaOH / methanol / 0.01 h / -20 °C

2: 99 percent / Et₃N / benzene / 1 h / 80 °C

3: 0.78 g / H₂ / 10percent Pd/C / methanol / 2.5 h / 25 °C / 760 Torr

4: methanol / 1.5 h / 25 °C

5: NaBH₄ / methanol / 0.5 h / 5 - 10 °C

6: 61 percent / NaBH₃CN, aq. AcOH / acetonitrile / 0.33 h / 25 °C

7: 38 percent / H₂ / 10percent Pd/C / methanol / 10 h / 25 °C / 760 Torr

8: 45 percent / BOPCl, Et₃N / CH₂Cl₂ / 6 h / 25 °C

With sodium hydroxide; sodium tetrahydroborate; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium cyanoborohydride; acetic acid; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile; benzene;

DOI:10.1016/0968-0896(95)00183-2

upstream raw materials:

pyrimidoblamic acid

(S)-2-Methylamino-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester

trityl chloride

1,N^α-bis-benzyloxycarbonyl-histidine methyl ester

Downstream raw materials:

N^α-[(tert-butyloxy)carbonyl]-N^β-[3(S)-[4-amino-6-[[[methyl-N-1-(S)-(((4(S)-[({1(S)-[({2-[4'-({[3-(dimethylsulfonio)-1-propyl]amino}carbonyl)-2',4-bithiazol-2-yl]-1-ethyl}amino)carbonyl]-2(R)-hydroxy-1-propyl}amino)carbonyl]-3(S)-hydroxy-2(R)-pe...

(S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid

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