Trifluoroacetic acid → HCID 21905108, compound

HRID 1247326Notes

Reaction equation

HRID 1247326 reaction equation
C(OC(=O)[NH:7][CH:8]([C:15](=[O:26])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O.C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[NH2:7][CH:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)=[O:26]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 69290327HCID 69290327, compound

Product 1

HCID 21905108HCID 21905108, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of give (RS)-[(4-cyano-benzylcarbamoyl)-phenyl-methyl]-carbamic acid tert-butyl ester (0.77 g, example 86.1) in dichloromethane (20 ml) was cooled to 0° C. and treated with trifluoro acetic acid (5 ml). The reaction mixture was stirred at rt for 5 hrs, then diluted with dichloromethane, cooled to 0° C. and brought to pH 9 by dropwise addition of saturated aqueous Na2CO3. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated to give (RS)-2-amino-N-(4-cyano-benzyl)-2-phenyl-acetamide (0.56 g). Off-white amorphous solid. MS 266.2 ([M+H]+)

Workup

  1. temperaturecooled to 0° C.
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b0a39bddf4ef4555a6044a8867d3d90d
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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