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1,2-Dichloroethane → tert-Butyl {2-[(1-hydroxy-2-methylpropan-2-yl)amino]-2-oxo-1-[3-(trifluoromethyl)phenyl]ethyl}-carbamate

HRID 574149
Notes
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Reaction equation

HRID 574149 reaction equation
C(Cl)CCl.[C:5]([O:9][C:10]([NH:12][CH:13]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)[C:14](O)=[O:15])=[O:11])([CH3:8])([CH3:7])[CH3:6].C1C=CC2N(O)N=NC=2C=1.[NH2:37][C:38]([CH3:42])([CH3:41])[CH2:39][OH:40]>CN(C=O)C>[C:5]([O:9][C:10](=[O:11])[NH:12][CH:13]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:24])([F:26])[F:25])[CH:18]=1)[C:14]([NH:37][C:38]([CH3:42])([CH3:41])[CH2:39][OH:40])=[O:15])([CH3:6])([CH3:7])[CH3:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 118072-Amino-2-methyl-1-propanolHCID 757711-HydroxybenzotriazoleHCID 223091762-{[(Tert-butoxy)carbonyl]amino}-2-[3-(trifluoromethyl)phenyl]acetic acid

Product 1

HCID 66807299tert-Butyl {2-[(1-hydroxy-2-methylpropan-2-yl)amino]-2-oxo-1-[3-(trifluoromethyl)phenyl]ethyl}-carbamate

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent2×

Procedure

360 mg (1.88 mmol) of EDC were added to a mixture of 400 mg (1.25 mmol) of [(tert-butoxycarbonyl)amino][3-(trifluoromethyl)phenyl]acetic acid and 254 mg (1.88 mmol) of HOBt in 10 ml of DMF, and the mixture was stirred at RT for 20 min. The resulting solution was added dropwise to a solution of 168 mg (1.88 mmol) of 2-amino-2-methyl-1-propanol in 2 ml of DMF. The reaction mixture was stirred at RT for 20 min. For purification, 1 ml of 1N hydrochloric acid was added and the entire reaction mixture was separated by preparative HPLC [Method 6]. The appropriate fraction was concentrated on a rotary evaporator and the residue was dried under high vacuum. This gave 364 mg (74% of theory) of the title compound.

Workup

  1. stirringThe reaction mixture was stirred at RT for 20 min
  2. customFor purification, 1 ml of 1N hydrochloric acid
  3. additionwas added
  4. customthe entire reaction mixture
  5. customwas separated by preparative HPLC [Method 6]
  6. concentrationThe appropriate fraction was concentrated on a rotary evaporator
  7. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-bb5dc7cceb034d738b5f7ca68756e82f
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