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Acetyl chloride → tert-Butyl {2-(acetylamino)-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

HRID 220637
Notes
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Reaction equation

HRID 220637 reaction equation
[NH2:1][CH2:2][CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1.C(N(CC)C(C)C)(C)C.[C:31](Cl)(=[O:33])[CH3:32]>ClCCl.C(OCC)(=O)C>[C:31]([NH:1][CH2:2][CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1)(=[O:33])[CH3:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 43094068tert-butyl N-{2-amino-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

Product 1

HCID 59536855tert-Butyl {2-(acetylamino)-1-[3-(trifluoromethyl)phenyl]ethyl}carbamateYield 100%

Reagents, catalysts & solvents 2

HCID 6344Dichloromethane
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

Of the compound from Example 22A, 75 mg (0.25 mmol) were introduced in 2.5 ml of dichloromethane together with 60 μl (0.35 mmol) of N,N-diisopropylethylamine and admixed at RT with 21 μl (0.30 mmol) of acetyl chloride. The mixture was stirred at RT for 1 h. The reaction mixture was diluted with ethyl acetate and washed in succession twice each with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, and then with saturated aqueous sodium chloride solution, dried over sodium sulphate and freed from the solvent on a rotary evaporator. Further drying in an HV gave 88 mg of the title compound (100% of theory).

Workup

  1. washwashed in succession twice each with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialwith saturated aqueous sodium chloride solution, dried over sodium sulphate
  3. customfreed from the solvent on a rotary evaporator
  4. customFurther drying in an HV

Sources & evidence

ORD record
ord-dc82cc01f719425f882f51edede579f9
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08202895B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes