Trimethylsilyldiazomethane → HCID 86597100, compound

HRID 1743238Notes

Reaction equation

HRID 1743238 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[CH2:8]([C@@:15]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])([CH2:20][CH:21]=[CH2:22])[CH2:16][C:17]([OH:19])=[O:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCCCCC.CO>[CH2:8]([C@@:15]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])([CH2:20][CH:21]=[CH2:22])[CH2:16][C:17]([O:19][CH3:1])=[O:18])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 67136375HCID 67136375, compound

Product 1

HCID 86597100HCID 86597100, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

A total of 5 ml of a 2 molar solution of trimethylsilyldiazomethane in hexane is added in portions to a solution of 490 mg of (S)-2-benzyl-2-tert-butoxycarbonylaminopent-4-enecarboxylic 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: methylene chloride:methanol=95:5).

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: methylene chloride:methanol=95:5)

Sources & evidence

ORD record
ord-9a1ee2e683344cc08e45783a72294586
Source dataset
uspto-grants-2006_03
Patent number
US07008957B2

Reaction notes

Loading…