(S)-tert-butyl 2-((S)-1-cyano-2-(4-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethylcarbamoyl)piperidine-1-carboxylate → (S)-N-((S)-1-Cyano-2-(4-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethyl)piperidine-2-carboxamide

HRID 600328Notes

Reaction equation

HRID 600328 reaction equation
[C:1]([C@@H:3]([NH:22][C:23]([C@@H:25]1[CH2:30][CH2:29][CH2:28][CH2:27][N:26]1C(OC(C)(C)C)=O)=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17](=[O:19])[N:16]([CH3:20])[C:15]=3[CH:21]=2)=[CH:7][CH:6]=1)#[N:2]>C(O)=O>[C:1]([C@@H:3]([NH:22][C:23]([C@@H:25]1[CH2:30][CH2:29][CH2:28][CH2:27][NH:26]1)=[O:24])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17](=[O:19])[N:16]([CH3:20])[C:15]=3[CH:21]=2)=[CH:9][CH:10]=1)#[N:2]

Participants

3

Reactant 1

HCID 57999653(S)-tert-butyl 2-((S)-1-cyano-2-(4-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethylcarbamoyl)piperidine-1-carboxylate

Product 1

HCID 57999646(S)-N-((S)-1-Cyano-2-(4-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethyl)piperidine-2-carboxamideYield 66%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of (S)-tert-butyl 2-((S)-1-cyano-2-(4-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethylcarbamoyl)piperidine-1-carboxylate (87 mg) in formic acid (1 mL) was stirred at 50° C. for 15 min. The solvent was removed in vacuo and the residue was purified by flash silica chromatography eluting with 1:29 ammonia in methanol/DCM to give a white solid, which was triturated with diethyl ether to give the title compound (46 mg) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash silica chromatography
  3. washeluting with 1:29 ammonia in methanol/DCM
  4. customto give a white solid, which
  5. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-1cbb48b5415e4e9c8f13aa8b1ef8feb5
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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