Water → 2-Piperidinecarboxamide, N-[(1S)-6-mercapto-1-[(phenylamino)carbonyl]hexyl]-6-oxo-, (2S)-

HRID 1422881Notes

Reaction equation

HRID 1422881 reaction equation
[OH-].[Na+].[O:3]=[C:4]1[NH:9][C@H:8]([C:10]([NH:12][C@H:13]([C:23](=[O:31])[NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][S:19]C(=O)C)=[O:11])[CH2:7][CH2:6][CH2:5]1.O>CCO>[SH:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]([NH:12][C:10]([C@@H:8]1[CH2:7][CH2:6][CH2:5][C:4](=[O:3])[NH:9]1)=[O:11])[C:23](=[O:31])[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 71506894HCID 71506894, compound

Product 1

HCID 715387462-Piperidinecarboxamide, N-[(1S)-6-mercapto-1-[(phenylamino)carbonyl]hexyl]-6-oxo-, (2S)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2N solution of NaOH (7.0 mmol) was added to a solution of thioacetic acid S—{(S)-6-[((S)-6-oxo-piperidine-2-carbonyl)-amino]-6-phenylcarbamoyl-hexyl}ester (0.95 mmol) in EtOH (13 ml). The reaction mixture was stirred at RT overnight and then poured into water and extracted with AcOEt, washed with water, brine and finally dried over Na2SO4. Removal of the solvent under reduced pressure led to the desired adduct, which was purified through HPLC.

Workup

  1. extractionextracted with AcOEt
  2. washwashed with water, brine
  3. dry with materialfinally dried over Na2SO4
  4. customRemoval of the solvent under reduced pressure
  5. customwas purified through HPLC

Sources & evidence

ORD record
ord-d7ce9162b904417ea3458f4e33a379d9
Source dataset
uspto-grants-2015_01
Patent number
US08927533B2

Reaction notes

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