Acetic Acid → HCID 91000600, compound

HRID 1743271Notes

Reaction equation

HRID 1743271 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@:9]1([CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])=[O:29])[CH2:24][CH2:23]2)[C:16](=[O:17])[N:15]2[C@@H:11]([S:12][CH2:13][C@H:14]2[C:18]([OH:20])=[O:19])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:37](OCC)C.C[Si](C=[N+]=[N-])(C)C.C(O)(=O)C>CO.CCCCCC>[C:1]([O:5][C:6]([NH:8][C@@:9]1([CH2:21][CH:22]2[CH2:23][CH2:24][N:25]([C:28]([O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])=[O:29])[CH2:26][CH2:27]2)[C:16](=[O:17])[N:15]2[C@@H:11]([S:12][CH2:13][C@H:14]2[C:18]([O:20][CH3:37])=[O:19])[CH2:10]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 67137775HCID 67137775, compound

Product 1

HCID 91000600HCID 91000600, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

497 mg of (3R,6R,7aS)-6-tert-butoxycarbonylamino-5-oxo-6-[1-(2-trimethylsilanylethoxycarbonyl)piperidin-4-ylmethyl]hexahydropyrrolo[2,1-b]thiazole-3-carboxylic acid were dissolved in 8 ml of methanol and 8 ml of diethyl ether and cooled to 0° C. 914 μl of a 1 N solution of trimethylsilyldiazomethane in hexane were added dropwise. The mixture was stirred for 1 h and then 1 ml of acetic acid was added dropwise. After 1 h, the solvents were removed in vacuo, and the residue was purified by chromatography on silica gel.

Workup

  1. waitAfter 1 h
  2. customthe solvents were removed in vacuo
  3. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a3bc41c1cb7d487d892199482939d9c3
Source dataset
uspto-grants-2006_03
Patent number
US07008957B2

Reaction notes

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