Trimethylsilyldiazomethane → HCID 57242472, compound

HRID 1872815Notes

Reaction equation

HRID 1872815 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][C@H:7]([NH:29][C:30]([C:32]1[CH:33]=[N:34][C:35]2[C:40]([CH:41]=1)=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:31])[C:8]([O:10][C@@H:11]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:12][C:13]([NH2:15])=[O:14])=[O:9])([OH:3])=[O:2].[CH3:42][Si](C=[N+]=[N-])(C)C>CO.CCCCCC>[CH3:42][O:2][C:1]([CH2:4][CH2:5][CH2:6][C@H:7]([NH:29][C:30]([C:32]1[CH:33]=[N:34][C:35]2[C:40]([CH:41]=1)=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:31])[C:8]([O:10][C@@H:11]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:12][C:13]([NH2:15])=[O:14])=[O:9])=[O:3]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 57199585HCID 57199585, compound

Product 1

HCID 57242472HCID 57242472, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

To a solution of (3S)-3-[(2S)-5-carboxy-2-{(3-quinolyl)carbonylamino}pentanoyl]oxyhexadecanamide (100 mg) in methanol (10 ml) was added 2M solution of trimethylsilyldiazomethane in hexane (2 ml) at room temperature. After being stirred at the same temperature for 2 days, the solvent was removed under reduced pressure and the resulting solid was triturated with ethyl ether to give (3S)-3-[(2S)-5-methoxycarbonyl-2-{(3-quinolyl)carbonylamino}pentanoyl]oxyhexadecanamide (68.4 mg).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe resulting solid was triturated with ethyl ether

Sources & evidence

ORD record
ord-b20d3d942f2542718052dd5e0e768d03
Source dataset
uspto-grants-2000_08
Patent number
US06110933

Reaction notes

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