HCID 140606942, compound → HCID 86683836, compound

HRID 572582Notes

Reaction equation

HRID 572582 reaction equation
[NH2:1]/[C:2](=[N:19]\[O:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])=[C:25]([C:36]([F:39])([F:38])[F:37])[CH:24]=1)=O)/[C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])=[CH:5][CH:4]=1>C1(C)C=CC=CC=1>[CH3:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:26]1[CH:27]=[CH:28][C:23]([C:21]2[O:20][N:19]=[C:2]([C:3]3[CH:4]=[CH:5][C:6]([C@H:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:17])[CH3:15])[CH3:10])=[CH:7][CH:8]=3)[N:1]=2)=[CH:24][C:25]=1[C:36]([F:39])([F:37])[F:38]

Participants

3

Reactant 1

HCID 140606942HCID 140606942, compound

Product 1

HCID 86683836HCID 86683836, compoundYield 116%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In a round bottom flask (500 ml), put under nitrogen atmosphere, tert-butyl [(1R)-1-(4-{(Z)-amino[({[2′-methyl-2-(trifluoromethyl)biphenyl-4-yl]carbonyl}oxy)imino]methyl}phenyl)ethyl]carbamate (17 g; 31.39 mmol; 1.0 eq.) was suspended in toluene (170 ml), and then heated at 100° C. After one night, the reaction mixture was concentrated under reduced pressure to give the title compound as a pale yellow oil (19.06 g, quantitative yield). This compound was used in the next step without further purification. LC/MS (Method B): 582.4 (M+AcO)−. HPLC (Method A) Rt 6.57 min (Purity: 99.1%)

Workup

  1. customIn a round bottom flask (500 ml), put under nitrogen atmosphere
  2. waitAfter one night
  3. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-428f4650fc7b43cb94a14f20732be48e
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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