Trimethylsilyldiazomethane → HCID 69795109, compound

HRID 1743239Notes

Reaction equation

HRID 1743239 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[CH2:8]([C@:15]1([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:22](=[O:23])[N:21]2[C@@H:17]([S:18][CH2:19][C@H:20]2[C:24]([OH:26])=[O:25])[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCCCCC.CO>[CH2:8]([C@:15]1([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:22](=[O:23])[N:21]2[C@@H:17]([S:18][CH2:19][C@H:20]2[C:24]([O:26][CH3:1])=[O:25])[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 67136426HCID 67136426, compound

Product 1

HCID 69795109HCID 69795109, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

A total of 1.5 ml of a 2 molar solution of trimethylsilyldiazomethane in hexane is added in portions to a solution of 250 mg of (3R,6R,7aS)-6-benzyl-6-tert-butoxycarbonylamino-5-oxohexahydropyrrolo[2,1-b]thiazole-3-carboxylic acid in 8 ml of methanol while stirring at room temperature. After the reaction is complete, the excess trimethylsilyldiazomethane is destroyed by dropwise addition of glacial acetic acid, and the volatile constituents are stripped off in a rotary evaporator at 40° C. The residue is purified on a column (silica gel, mobile phase:ethyl acetate:n-heptane=1:1.5).

Workup

  1. customthe excess trimethylsilyldiazomethane is destroyed by dropwise addition of glacial acetic acid
  2. customthe volatile constituents are stripped off in a rotary evaporator at 40° C
  3. customThe residue is purified on a column (silica gel, mobile phase:ethyl acetate:n-heptane=1:1.5)

Sources & evidence

ORD record
ord-e1458947829447c7a67df207ccaa5a4b
Source dataset
uspto-grants-2006_03
Patent number
US07008957B2

Reaction notes

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