Acetic Acid → HCID 91250266, compound

HRID 1743263Notes

Reaction equation

HRID 1743263 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@:9]1([CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])=[O:28])[CH2:23][CH2:22]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].[CH2:36](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([CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])=[O:28])[CH2:23][CH2:22]2)[C:16](=[O:17])[N:15]2[C@@H:11]([S:12][CH2:13][C@H:14]2[C:18]([O:20][CH3:36])=[O:19])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 67136328HCID 67136328, compound

Product 1

HCID 91250266HCID 91250266, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

223 mg of (3R,6S,7aS)-6-tert-butoxycarbonylamino-5-oxo-6-[1-(2-trimethylsilanylethoxycarbonyl)piperidin-4-yl]hexahydropyrrolo[2,1-b]thiazole-3-carboxylic acid were dissolved in 10 ml of methanol and 10 ml of diethyl ether and cooled to 0° C. 400 μl portions of a 1 N solution of trimethylsilyldiazomethane in hexane were added dropwise twice at an interval of 1.5 h. The mixture was stirred for 2 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 chromatogrpahy on silica gel.

Workup

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

Sources & evidence

ORD record
ord-581ca427570741af957e159d4c93fb84
Source dataset
uspto-grants-2006_03
Patent number
US07008957B2

Reaction notes

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