(3R,6S,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid

Base Information

• Chemical Name: (3R,6S,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid
• CAS No.: 188200-08-0
• Molecular Formula: C₁₅H₁₈N₂O₅S₂
• Molecular Weight: 370.45

Synonyms:(3R,6S,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid

Chemical Property of (3R,6S,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid

Chemical Property:

Purity/Quality:

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Technology Process of (3R,6S,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid

There total 9 articles about (3R,6S,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic 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: 89.0%

(3R,6S,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester → (3R,6S,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid (188200-08-0)

Guidance literature:

With sodium hydroxide; In methanol; water; at 0 ℃;

DOI:10.1016/S0960-894X(97)00004-8

Reference yield:

Boc-Glu(OBzl)-OH (13574-13-5) → (3R,6S,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid (188200-08-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) CDI / 1.) THF, 0 deg C to room temperature, 2.) 0 deg C to room temperature

2: H₂ / Pd/C / tetrahydrofuran

3: 78 percent / EDC, DMAP / acetonitrile / Ambient temperature

4: 75 percent / Et₃SiH / Pd/C / acetone / 2 h / Ambient temperature

5: 78 percent / pyridine, 4A molecular sieves / 1.) room temeprature, 4 h, 2.) reflux, 18 h

6: 1.) CDI / 1.) THF, 0 deg C to room temperature, 2.) 0 deg C to room temperature

7: 81 percent / CH₂Cl₂ / 0 - 20 °C

8: 50 percent / collidine / 0 - 20 °C

9: 89 percent / NaOH / methanol; H₂O / 0 °C

With pyridine; 2,3,5-trimethyl-pyridine; triethylsilane; dmap; sodium hydroxide; 4 A molecular sieve; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile;

DOI:10.1016/S0960-894X(97)00004-8

Reference yield:

N-tert-butoxycarbonylglutamic acid methyl ester (72086-72-7) → (3R,6S,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid (188200-08-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 78 percent / EDC, DMAP / acetonitrile / Ambient temperature

2: 75 percent / Et₃SiH / Pd/C / acetone / 2 h / Ambient temperature

3: 78 percent / pyridine, 4A molecular sieves / 1.) room temeprature, 4 h, 2.) reflux, 18 h

4: 1.) CDI / 1.) THF, 0 deg C to room temperature, 2.) 0 deg C to room temperature

5: 81 percent / CH₂Cl₂ / 0 - 20 °C

6: 50 percent / collidine / 0 - 20 °C

7: 89 percent / NaOH / methanol; H₂O / 0 °C

With pyridine; 2,3,5-trimethyl-pyridine; triethylsilane; dmap; sodium hydroxide; 4 A molecular sieve; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In methanol; dichloromethane; water; acetone; acetonitrile;

DOI:10.1016/S0960-894X(97)00004-8

upstream raw materials:

Boc-Glu(OBzl)-OH

N-tert-butoxycarbonylglutamic acid methyl ester

N^α-tert-butyloxycarbonyl-γ-benzyloxycarbonyl-L-glutamic acid methyl ester

N-Boc-BTD

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