Trimethylsilyldiazomethane → HCID 59722694, compound

HRID 1664857Notes

Reaction equation

HRID 1664857 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[C:8]([O:12][C:13]([NH:15][C@@H:16]1[CH2:22][CH2:21][C@@H:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=2[F:30])[CH2:19][N:18]2[C:31]([C:34]([OH:36])=[O:35])=[CH:32][N:33]=[C:17]12)=[O:14])([CH3:11])([CH3:10])[CH3:9]>ClCCl.CO>[C:8]([O:12][C:13]([NH:15][C@@H:16]1[CH2:22][CH2:21][C@@H:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=2[F:30])[CH2:19][N:18]2[C:31]([C:34]([O:36][CH3:1])=[O:35])=[CH:32][N:33]=[C:17]12)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 2

HCID 167693Trimethylsilyldiazomethane2×HCID 67439630HCID 67439630, compound

Product 1

HCID 59722694HCID 59722694, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

(Trimethylsilyl)diazomethane (2.0 M in ether; 173 μL, 0.35 mmol) was added to a solution of (6S,9R)-9-[(tert-butoxycarbonyl)amino]-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepine-3-carboxylic acid (47 mg, 0.12 mmol) in dichloromethane (1.5 mL) and methanol (0.5 mL). After 1 h, additional (trimethylsilyl)diazomethane (2.0 M in diethyl ether; 50 μL, 0.10 mmol) was added. After 4 h, the reaction mixture was concentrated. MS 422.2 (M+1).

Workup

  1. waitAfter 4 h
  2. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-10a3a0f15d4b4ad88b8098f48c2d77e7
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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