N^α-<6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carbonyl>-erithro-β-tert-butoxy-L-histidine tert-butyl ester

Base Information

• Chemical Name: N^α-<6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carbonyl>-erithro-β-tert-butoxy-L-histidine tert-butyl ester
• CAS No.: 118823-75-9
• Molecular Formula: C₃₆H₄₂ClN₉O₉S₂
• Molecular Weight: 844.369

Synonyms:

Chemical Property of N^α-<6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carbonyl>-erithro-β-tert-butoxy-L-histidine tert-butyl ester

Chemical Property:

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Technology Process of N^α-<6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carbonyl>-erithro-β-tert-butoxy-L-histidine tert-butyl ester

There total 13 articles about N^α-<6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carbonyl>-erithro-β-tert-butoxy-L-histidine 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: 63.0%

6-{[[(S)-2-Carbamoyl-2-(2-nitro-phenylsulfanylamino)-ethyl]-(2-nitro-phenylsulfanyl)-amino]-methyl}-4-chloro-pyridine-2-carboxylic acid (118823-74-8) + erithro-β-tert-butoxy-L-histidine-tert-butyl ester hydrochloride (101485-30-7,118130-93-1) → Nα-<6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carbonyl>-erithro-β-tert-butoxy-L-histidine tert-butyl ester (118823-75-9)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; 0 deg C, then RT, 12 h;

DOI:10.1016/S0040-4020(88)90018-X

Reference yield:

dimethyl 4-chloro-2,6-pyridinedicarboxylate (5371-70-0) → Nα-<6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carbonyl>-erithro-β-tert-butoxy-L-histidine tert-butyl ester (118823-75-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / NaBH₄ / methanol / 0 deg C to RT, 3 h

2: 1.) (COCl)2, 2.) Et₃N / 1.) DMSO, CH₂Cl₂, -30 deg C, 20 min, 2.) -60 deg C, 25 min, then RT

3: molecular sieve 3A / acetonitrile / 12 h / Ambient temperature

4: NaBH₄ / methanol / 0 deg C, then RT, 20 min

5: 90 percent / trifluoroacetic acid, Et₃N / CH₂Cl₂ / 0 deg C, 30 min, then RT, 6 h

6: LiOH / tetrahydrofuran

7: 63 percent / DCC, HOBt, N-methylmorpholine / dimethylformamide / 0 deg C, then RT, 12 h

With 4-methyl-morpholine; lithium hydroxide; sodium tetrahydroborate; oxalyl dichloride; 3 A molecular sieve; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(88)90018-X

Reference yield:

methyl 4-chloro-6-hydroxymethylpyridine-2-carboxylate (109880-43-5) → Nα-<6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carbonyl>-erithro-β-tert-butoxy-L-histidine tert-butyl ester (118823-75-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) (COCl)2, 2.) Et₃N / 1.) DMSO, CH₂Cl₂, -30 deg C, 20 min, 2.) -60 deg C, 25 min, then RT

2: molecular sieve 3A / acetonitrile / 12 h / Ambient temperature

3: NaBH₄ / methanol / 0 deg C, then RT, 20 min

4: 90 percent / trifluoroacetic acid, Et₃N / CH₂Cl₂ / 0 deg C, 30 min, then RT, 6 h

5: LiOH / tetrahydrofuran

6: 63 percent / DCC, HOBt, N-methylmorpholine / dimethylformamide / 0 deg C, then RT, 12 h

With 4-methyl-morpholine; lithium hydroxide; sodium tetrahydroborate; oxalyl dichloride; 3 A molecular sieve; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(88)90018-X

upstream raw materials:

erythro-β-tert-Butoxy-L-histidine tert-butyl ester

6-{[[(S)-2-Carbamoyl-2-(2-nitro-phenylsulfanylamino)-ethyl]-(2-nitro-phenylsulfanyl)-amino]-methyl}-4-chloro-pyridine-2-carboxylic acid

dimethyl 4-chloro-2,6-pyridinedicarboxylate

methyl 4-chloro-6-hydroxymethylpyridine-2-carboxylate

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