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1,2-Dichloroethane → Ethyl 1-({[(tert-butoxycarbonyl)amino][3-(trifluoromethyl)phenyl]acetyl}amino)cyclopropanecarboxylate

HRID 574147
Notes
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Reaction equation

HRID 574147 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:23][C:24]1([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:26][CH2:25]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=1)[C:10]([NH:23][C:24]1([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:26][CH2:25]1)=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 386204Ethyl 1-aminocyclopropanecarboxylateHCID 223091762-{[(Tert-butoxy)carbonyl]amino}-2-[3-(trifluoromethyl)phenyl]acetic acid

Product 1

HCID 66801809Ethyl 1-({[(tert-butoxycarbonyl)amino][3-(trifluoromethyl)phenyl]acetyl}amino)cyclopropanecarboxylate

Reagents, catalysts & solvents

2
HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 500 mg (1.57 mmol) of [(tert-butoxycarbonyl)amino][3-(trifluoromethyl)-phenyl]acetic acid, 243 mg (1.88 mmol) of ethyl 1-aminocyclopropanecarboxylate, 450 mg (2.35 mmol) of EDC and 317 mg (2.35 mmol) of HOBt in 10 ml of DMF was stirred at RT overnight. The reaction mixture was diluted with ethyl acetate and washed twice with 1N hydrochloric acid and once with a saturated aqueous sodium bicarbonate solution. The organic phase was dried over sodium sulphate and then freed from the solvent on a rotary evaporator. The residue was dried under high vacuum. This gave 650 mg (96% of theory) of the title compound.

Workup

  1. washwashed twice with 1N hydrochloric acid and once with a saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customfreed from the solvent on a rotary evaporator
  4. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-bdcae72e96dc4e69890096b6d291c9c9
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09034855B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes