Dichloromethane → HCID 66727525, compound

HRID 559743Notes

Reaction equation

HRID 559743 reaction equation
[C:1]([CH:4]1[CH2:9][CH:8]([C@@H:10]([NH:13][C:14](=[O:16])[OH:15])[CH2:11][CH3:12])[CH2:7][CH2:6][NH:5]1)(=[O:3])[NH2:2].CCN([CH:23]([CH3:25])[CH3:24])C(C)C.[CH2:26]([O:33][C:34](Cl)=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH2:37](Cl)Cl>>[CH2:26]([O:33][C:34]([N:5]1[CH2:6][CH2:7][CH:8]([C@@H:10]([NH:13][C:14]([O:15][C:23]([CH3:24])([CH3:25])[CH3:37])=[O:16])[CH2:11][CH3:12])[CH2:9][CH:4]1[C:1](=[O:3])[NH2:2])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 86640803HCID 86640803, compound

Product 1

HCID 66727525HCID 66727525, compound

Procedure

To a chilled (0° C.) solution of [(S)-1-(2-carbamoyl-piperidin-4-yl)-propyl]-carbamic acid tent-butyl ester (780 mg, 2.73 mmol) in methylene chloride (25 mL) was added DIPEA (0.41 mL, 2.9 mmol) followed by benzylchloroformate (723 μL, 4.1 mmol). After 1 hour, the reaction was diluted with dichloromethane (200 mL), washed with saturated ammonium chloride, brine, dried over sodium sulfate, filtered and concentrated to afford 4-((S)-1-tert-butoxycarbonylamino-propyl)-2-carbamoyl-piperidine-1-carboxylic acid benzyl ester.

Workup

  1. washwashed with saturated ammonium chloride, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ad502be0bf634a4f87ccf5ab272a3a9d
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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