3-(Trifluoromethyl)benzoic acid → HCID 91334299, compound

HRID 2225278Notes

Reaction equation

HRID 2225278 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][C@H:3]1[C@@H:16]([OH:20])[CH:17]([CH3:19])[CH3:18].[F:21][C:22]([F:33])([F:32])[C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([OH:28])=O.[CH2:34]([N:36](C(C)C)CC)[CH3:35].CN(C([O:49]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[OH:20][C@H:16]([C@H:3]1[C@@H:2]([NH:1][C:35](=[O:49])[CH2:34][NH:36][C:26](=[O:28])[C:25]2[CH:29]=[CH:30][CH:31]=[C:23]([C:22]([F:21])([F:33])[F:32])[CH:24]=2)[CH2:7][CH2:6][C@@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:4]1)[CH:17]([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 99633-(Trifluoromethyl)benzoic acidHCID 521913N,N-Diethyl-2-propanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131726907HCID 131726907, compound

Product 1

HCID 91334299HCID 91334299, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl(1R,3R,4S)-4-amino-3-((S)-1-hydroxy-2-methylpropyl)cyclohexylcarbamate (300 mg, 1.05 mmol) in DMF (10 mL) was charged with 3-(trifluoromethyl)benzoic acid (330 mg, 1.26 mmol), N,N-diethylisopropylamine (0.2 mL, 1.26 mmol), and HATU (480 mg, 1.26 mmol). The reaction was stirred for 16 h at RT and then partitioned between EtOAc and sat. NaHCO3; the aqueous phase was back extracted with EtOAc. The organic phases were combined, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to afford tert-butyl(1R,3R,4S)-3-((S)-1-hydroxy-2-methylpropyl)-4-(2-(3-(trifluoromethyl)benzamido)acetamido)cyclohexylcarbamate. MS found: (M+H)+=516.

Workup

  1. custompartitioned between EtOAc and sat. NaHCO3
  2. extractionthe aqueous phase was back extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dfdf6152a6094b7c8ab7b1cd54cdc885
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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