Trifluoroacetic acid → HCID 68591310, compound

HRID 1994480Notes

Reaction equation

HRID 1994480 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:9][NH:10][CH2:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[C:22]1[CH:27]=[C:26]([CH:28]([CH3:30])[CH3:29])[CH:25]=[CH:24][C:23]=1[O:31][CH3:32])(C)(C)C.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[CH:28]([C:26]1[CH:25]=[CH:24][C:23]([O:31][CH3:32])=[C:22]([C:13]2[CH:14]=[CH:15][C:16]([C:18]([F:20])([F:21])[F:19])=[CH:17][C:12]=2[CH2:11][NH:10][CH2:9][C@@H:8]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH2:7])[CH:27]=1)([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 131727862HCID 131727862, compound

Product 1

HCID 68591310HCID 68591310, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl[(1R)-2-({[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}amino)-1-phenylethyl]carbamate (150 mg, 0.277 mmol) containing minor impurities in CH2Cl2 (10 mL) was added TFA (1 mL). The reaction was stirred at room temperature for 2 hours and then poured into 1 N NaOH (25 mL). The mixture was extracted with CH2Cl2 (3×25 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated. Purification of the resulting residue by flash chromatography with 0 to 10% MeOH/CH2Cl2 afforded (1R)—N2-{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-1-phenylethane-1,2-diamine. Rf=0.27 (10% MeOH/CH2Cl2). LCMS=443.4 (M+1)+.

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (3×25 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the resulting residue by flash chromatography with 0 to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-7458c4d7ae5849d2b4258a349286e4cc
Source dataset
uspto-grants-2010_01
Patent number
US07652049B2

Reaction notes

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