Chloroform → HCID 66637581, compound

HRID 1093923Notes

Reaction equation

HRID 1093923 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[C@@H:10]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:12][CH2:13]I)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(Cl)(Cl)Cl>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:23])[C@@H:10]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:12][CH2:13][N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 8082PiperidineHCID 11797018HCID 11797018, compound

Product 1

HCID 66637581HCID 66637581, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-t-butoxycarbonyl-(S)-2-amino-5-iodopentanoic acid benzyl ester(J.Org. Chem. 1998, 7875-7884)(100.8 mg, 0.23 mmol) in N,N-dimethylformamide (0.25 mL) was added piperidine (41.5 mg, 0.49 mmol) and the mixture was stirred for 3 hours at room temperature. To the reaction mixture was added chloroform (30 mL) and the mixture was washed with saturated aqueous sodium hydrogencarbonate solution (3×3 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum to obtain crude N-t-butoxycarbonyl-(S)-2-amino-5-(1-piperidinyl)pentanoic acid benzyl ester(83.8 mg) as a colorless oily material.

Workup

  1. washthe mixture was washed with saturated aqueous sodium hydrogencarbonate solution (3×3 mL)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-78d82368acdb444b97bd0887033db069
Source dataset
uspto-grants-2012_03
Patent number
US08133864B2

Reaction notes

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