Piperidine → HCID 10863399, compound

HRID 1386912Notes

Reaction equation

HRID 1386912 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:47])[C@H:7]([CH2:26][S:27][C:28]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[NH:8]C(OCC1C2CC3C(=CC=CC=3)C=2C=CC=1)=O)([CH3:4])[CH3:3].N1CCCCC1>CN(C=O)C>[CH3:4][C:2]([O:5][C:6](=[O:47])[C@H:7]([CH2:26][S:27][C:28]([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[NH2:8])([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 69624811HCID 69624811, compound

Product 1

HCID 10863399HCID 10863399, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-fluorenylmethoxycarbonyl-S-trityl-L-cysteine 1,1-dimethylethyl ester (640 mg, 1 mmol) in 5 mL of DMF was added 2 mL of piperidine. The solution was stirred for 20 min., and the solvent was evaporated. The residual piperidine was removed by azeotroping the solid with DMF (3×20 mL) and drying under high vacuum for 1 hour to give S-trityl-L-cysteine 1,1-dimethylethyl ester as a solid. To this solid was added 5 mL of DMF followed by 1-(2-azidoethyl)cyclopentane carboxylic acid (6a) (183 mg, 1 mmol), HBTU (379 mg, 1 mmol), and DIPEA (0.18 mL, 1 mmol). The resulting solution was stirred for 5 hours, and the solvent was removed under high vacuum. The residue was purified by silica gel column chromatography usilng ethylacetate/hexanes (15/85) as eluent, to afford 500 mg (86%) of N-[[1-(2-azidoethyl)cyclopentyl]carbonyl]-S-triphenylmethyl-L-cysteinie 1,1-dimethylethyl ester.

Workup

  1. customthe solvent was evaporated
  2. customThe residual piperidine was removed
  3. customby azeotroping the solid with DMF (3×20 mL)
  4. customdrying under high vacuum for 1 hour

Sources & evidence

ORD record
ord-882061d0c9ff44b58c07439bdcde399d
Source dataset
uspto-grants-2001_07
Patent number
US06265572B1

Reaction notes

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