(2S,4S)-2-{[(Pyridine-3-carbonyl)-amino]-methyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid 4-methoxy-benzyl ester

Base Information

• Chemical Name: (2S,4S)-2-{[(Pyridine-3-carbonyl)-amino]-methyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid 4-methoxy-benzyl ester
• CAS No.: 175846-09-0
• Molecular Formula: C₃₉H₃₇N₃O₄S
• Molecular Weight: 643.806

Synonyms:(2S,4S)-2-{[(Pyridine-3-carbonyl)-amino]-methyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid 4-methoxy-benzyl ester

Chemical Property of (2S,4S)-2-{[(Pyridine-3-carbonyl)-amino]-methyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid 4-methoxy-benzyl ester

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Technology Process of (2S,4S)-2-{[(Pyridine-3-carbonyl)-amino]-methyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid 4-methoxy-benzyl ester

There total 9 articles about (2S,4S)-2-{[(Pyridine-3-carbonyl)-amino]-methyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid 4-methoxy-benzyl 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: 70.0%

pyridine-3-carbonyl chloride hydrochloride (20260-53-1) + (2S,4S)-2-aminomethyl-1-p-methoxybenzyloxycarbonyl-4-tritylthiopyrrolidine (148016-92-6) → (2S,4S)-2-{[(Pyridine-3-carbonyl)-amino]-methyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid 4-methoxy-benzyl ester (175846-09-0)

Guidance literature:

With triethylamine; In dichloromethane; at -30 ℃; for 0.333333h;

DOI:10.7164/antibiotics.49.199

Reference yield:

(R)-4-hydroxy-L-proline ethyl ester (1499-56-5,775275-31-5,790644-51-8,754962-86-2) → (2S,4S)-2-{[(Pyridine-3-carbonyl)-amino]-methyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid 4-methoxy-benzyl ester (175846-09-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 32.48 g / triethylamine / methanol / 0.33 h

2: 98 percent / triethylamine / CH₂Cl₂ / 0.25 h / -30 °C

3: 1) sodium hydride / 1) DMF, room temperature, 1 h, 2) 60 deg C, 30 min

4: 68 percent / LiBH₄ / tetrahydrofuran / 0.5 h / 60 °C

5: 87.4 percent / triethylamine / CH₂Cl₂ / 0.33 h / -30 °C

6: 78.1 percent / dimethylformamide / 1 h / 100 °C

7: 78 percent / H₂NNH₂*H₂O / CH₂Cl₂; methanol / 5 h / 60 °C

8: 70 percent / triethylamine / CH₂Cl₂ / 0.33 h / -30 °C

With lithium borohydride; sodium hydride; hydrazine hydrate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.49.199

Reference yield:

(2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester (104773-44-6) → (2S,4S)-2-{[(Pyridine-3-carbonyl)-amino]-methyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid 4-methoxy-benzyl ester (175846-09-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / triethylamine / CH₂Cl₂ / 0.25 h / -30 °C

2: 1) sodium hydride / 1) DMF, room temperature, 1 h, 2) 60 deg C, 30 min

3: 68 percent / LiBH₄ / tetrahydrofuran / 0.5 h / 60 °C

4: 87.4 percent / triethylamine / CH₂Cl₂ / 0.33 h / -30 °C

5: 78.1 percent / dimethylformamide / 1 h / 100 °C

6: 78 percent / H₂NNH₂*H₂O / CH₂Cl₂; methanol / 5 h / 60 °C

7: 70 percent / triethylamine / CH₂Cl₂ / 0.33 h / -30 °C

With lithium borohydride; sodium hydride; hydrazine hydrate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.49.199

upstream raw materials:

pyridine-3-carbonyl chloride hydrochloride

(2S,4S)-2-aminomethyl-1-p-methoxybenzyloxycarbonyl-4-tritylthiopyrrolidine

(R)-4-hydroxy-L-proline ethyl ester

(2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester

Downstream raw materials:

(2S,4S)-4-Mercapto-2-{[(pyridine-3-carbonyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid 4-methoxy-benzyl ester

(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-((3S,5S)-1-(4-methoxy-benzyloxycarbonyl)-5-{[(pyridine-3-carbonyl)-amino]-methyl}-pyrrolidin-3-ylsulfanyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

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