3-(Trifluoromethyl)benzoic acid → HCID 86596889, compound

HRID 1455431Notes

Reaction equation

HRID 1455431 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C@H:7]2[CH2:12][CH2:11][C@@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][C@H:8]2[CH2:21][S:22]([CH:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])[C:3]1=[O:28].[F:29][C:30]([F:41])([F:40])[C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34](O)=[O:35].C(N(C(C)C)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:25]([S:22]([CH2:21][C@H:8]1[C@@H:7]([N:4]2[CH2:5][CH2:6][C@H:2]([NH:1][C:34](=[O:35])[C:33]3[CH:37]=[CH:38][CH:39]=[C:31]([C:30]([F:29])([F:40])[F:41])[CH:32]=3)[C:3]2=[O:28])[CH2:12][CH2:11][C@@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:17])[CH3:18])[CH2:9]1)(=[O:24])=[O:23])([CH3:26])[CH3:27]

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 86596890HCID 86596890, compound

Product 1

HCID 86596889HCID 86596889, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A sample of tert-butyl (1R,3R,4S)-4-((S)-3-amino-2-oxopyrrolidin-1-yl)-3-(isopropylsulfonylmethyl)cyclohexylcarbamate (200 mg, 0.47 mmol) in DMF (10 mL) was charged with 3-(trifluoromethyl)benzoic acid (109 mg, 0.57 mmol), N,N-diethylisopropylamine (0.1 mL, 0.57 mmol), and HATU (216 mg, 0.57 mmol). The reaction was stirred for 48 h at RT and then partitioned between EtOAc and sat. NaHCO3; the aqueous phase was back extracted with EtOAc (1×). The organic phases were combined, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to afford tert-butyl (1R,3R,4S)-3-(isopropylsulfonylmethyl)-4-((S)-2-oxo-3-(3-(trifluoromethyl)benzamido)pyrrolidin-1-yl)cyclohexylcarbamate. MS found: (M+H)+=590.

Workup

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

Sources & evidence

ORD record
ord-55702eb01d4b46d1867617a7888bfd84
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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