Trimethylsilyldiazomethane → HCID 58638078, compound

HRID 1768475Notes

Reaction equation

HRID 1768475 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([CH3:27])[CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]([OH:26])=[O:25])[CH2:19][CH2:18]2)=[O:15])[C:11]([CH2:34][OH:35])([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:10]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:37]>C1C=CC=CC=1.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([CH3:27])[CH:17]2[CH2:18][CH2:19][N:20]([CH2:23][C:24]([O:26][CH3:37])=[O:25])[CH2:21][CH2:22]2)=[O:15])[C:11]([CH2:34][OH:35])([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 23614723HCID 23614723, compound

Product 1

HCID 58638078HCID 58638078, compound

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

To 30 mg (0.06 mmol) of amino acid 17-1 in 1:1 PhH/MeOH was added 120 μL (0.24 mmol) of TMS-diazomethane. After stirring for 2 h, the reaction was concentrated by rotary evaporation and the residue was purified by column chromatography on silica gel with 20:1:1 EtOH/NH4OH/H2O in EtOAc to provide 17-2 as a colorless film. Data for 17-2: 1HNMR (500 MHz, CDCl3) δ 7.4-7.2 (m, 5H), 7.1-6.9 (m, 3H), 6.3 (s, 1H), 5.45 (m, 1H), 4.8 (m, 1H), 4.6 (m, 1H), 4.4 (m, 1H), 4.0 (m, 1H), 3.75 (m, 1H), 3.7 (s, 3H), 3.2 (m, 2H), 3.05 (m, 2H), 2.9 (s, 3H), 2.3 (m, 2H), 2.0-1.8 (m, 3H), 1.7 (m, 1H) ppm. HRMS (ES) calc'd M+H for C27H31F2N3O4: 500.2356. Found: 500.2331.

Workup

  1. concentrationthe reaction was concentrated by rotary evaporation
  2. customthe residue was purified by column chromatography on silica gel with 20:1:1 EtOH/NH4OH/H2O in EtOAc
  3. customto provide 17-2 as a colorless film

Sources & evidence

ORD record
ord-b34c9de4a2564ad294abc4a09cb5ac1c
Source dataset
uspto-grants-2007_06
Patent number
US07235580B2

Reaction notes

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