Trifluoroacetic acid → HCID 69286611, compound

HRID 2225279Notes

Reaction equation

HRID 2225279 reaction equation
[OH:1][C@H:2]([C@H:6]1[C@@H:11]([NH:12][C:13](=[O:28])[CH2:14][NH:15][C:16](=[O:27])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[CH2:10][CH2:9][C@@H:8]([NH:29]C(=O)OC(C)(C)C)[CH2:7]1)[CH:3]([CH3:5])[CH3:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:29][C@@H:8]1[CH2:9][CH2:10][C@H:11]([NH:12][C:13](=[O:28])[CH2:14][NH:15][C:16](=[O:27])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[C@H:6]([C@@H:2]([OH:1])[CH:3]([CH3:4])[CH3:5])[CH2:7]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 91334299HCID 91334299, compound

Product 1

HCID 69286611HCID 69286611, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The entirety of tert-butyl(1R,3R,4S)-3-((S)-1-hydroxy-2-methylpropyl)-4-(2-(3-(trifluoromethyl)benzamido)acetamido)cyclohexylcarbamate prepared in previous Step (1 eq) in CH2Cl2 (20 mL) was added TFA (4 mL) at RT. The reaction was stirred for 5 h and concentrated in vacuo. The residue was partitioned between 1N NaOH (30 mL) and EtOAc (40 mL). The aqueous layer was extracted with EtOAc (2×50 mL) and the organic phases were combined, washed with brine (25 mL), dried (Na2SO4), filtered, and concentrated in vacuo to give N-(2-((1S,2R,4R)-4-amino-2-((S)-1-hydroxy-2-methylpropyl)cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide. MS found: (M+H)+=416.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between 1N NaOH (30 mL) and EtOAc (40 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
  4. washwashed with brine (25 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f37f65ea327e40e581dd55de7803f964
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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