Trimethylsilyldiazomethane → HCID 66757872, compound

HRID 917192Notes

Reaction equation

HRID 917192 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:20]([C:31]([OH:33])=[O:32])[CH2:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:34][Si](C=[N+]=[N-])(C)C>C1(C)C=CC=CC=1.CO>[CH3:34][O:32][C:31]([CH:20]1[CH2:19][N:18]([C:16]([O:15][CH2:14][CH:12]2[C:13]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)=[O:17])[CH2:23][CH2:22][N:21]1[C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])=[O:33]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 27567971-((tert-butoxy)carbonyl)-4-(((9H-fluoren-9-yl)methoxy)carbonyl)piperazine-2-carboxylic acid

Product 1

HCID 66757872HCID 66757872, compound

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Procedure

To a solution of piperazine-1,2,4-tricarboxylic acid 1-tert-butyl ester 4-(9H-fluoren-9-ylmethyl)ester (2.21 mmol) in toluene: methanol (9:1) was added equimolar trimethylsilyldiazomethane (2.0 M in hexanes) and the resulting mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo and purified using gradient elution from hexane/ethyl acetate (5%) to hexane/ethyl acetate (30%). ESI-MS m/z: 467 (M+1), UV retention time: 3.04 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified
  3. washelution from hexane/ethyl acetate (5%) to hexane/ethyl acetate (30%)

Sources & evidence

ORD record
ord-19eeafa532974dd4a782ed8a3b8d5d9d
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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