Triethylamine → Methyl N-({3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}carbonyl)glycinate

HRID 876314Notes

Reaction equation

HRID 876314 reaction equation
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][NH:14][CH2:13][CH:12]([NH:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:11]2)=[CH:6][CH:5]=1.[O:27]=[C:28]=[N:29][CH2:30][C:31]([O:33][CH3:34])=[O:32].C(N(CC)CC)C>C1COCC1>[C:18]1([C:17]([NH:16][CH:12]2[CH2:11][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:25])[F:26])=[CH:9][CH:8]=3)[CH2:15][N:14]([C:28]([NH:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[O:27])[CH2:13]2)=[O:24])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2769479Methyl 2-isocyanatoacetateHCID 66701272N-{5-[4-(trifluoromethoxy)phenyl]piperidin-3-yl}benzamide

Product 1

HCID 66761299Methyl N-({3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}carbonyl)glycinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

70 mg (0.19 mmol) of N-{5-[4-(trifluoromethoxy)phenyl]piperidin-3-yl}benzamide were initially charged in 2.5 ml of THF, and 22 mg (0.19 mmol) of methyl N-(oxomethylidene)glycinate and 29 μl (0.21 mmol) of triethylamine were added. The mixture was stirred at RT overnight. The reaction mixture was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 76 mg (82% of theory)

Workup

  1. customThe reaction mixture was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-660cc08873554ead81f1d12e68096090
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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