Sodium Carbonate → Methyl (2s)-phenyl[4-[4-[[[4'-(trifluoromethyl)-2-biphenylyl]carbonyl]amino]phenyl]-1-piperidinyl]acetate

HRID 1989859Notes

Reaction equation

HRID 1989859 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[C:17]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:15])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[Na+].[Na+].Br[CH:39]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:40]([O:42][CH3:43])=[O:41]>CN(C=O)C>[C:44]1([CH:39]([N:1]2[CH2:6][CH2:5][CH:4]([C:7]3[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:22]4[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:27]=4)=[O:15])=[CH:9][CH:8]=3)[CH2:3][CH2:2]2)[C:40]([O:42][CH3:43])=[O:41])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 22499368N-[4-(4-piperidinyl)phenyl]-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamide

Product 1

HCID 17989467Methyl (2s)-phenyl[4-[4-[[[4'-(trifluoromethyl)-2-biphenylyl]carbonyl]amino]phenyl]-1-piperidinyl]acetateYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of intermediate (10) (0.007 mol) and Na2CO3 (0.007 mol) in DMF (50 ml) was stirred at room temperature. Methyl 2-bromo-2-phenylacetate (0.007 mol) was added dropwise. The mixture was stirred for 3 hours. The solvent was evaporated. The residue was triturated under hexane, filtered off and dried, yielding 3.37 g of methyl α-phenyl-4-[4-[[[4′-(trifluoromethyl)[1,1′-biphenyl]-2-yl]carbonyl]amino]-phenyl]-1-piperidineacetate (intermediate 11, mp. 138° C.).

Workup

  1. stirringThe mixture was stirred for 3 hours
  2. customThe solvent was evaporated
  3. customThe residue was triturated under hexane
  4. filtrationfiltered off
  5. customdried

Sources & evidence

ORD record
ord-38b6e5b61bd140fcba318816cc0f3e1b
Source dataset
uspto-grants-2010_01
Patent number
US07642378B2

Reaction notes

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