Formaldehyde → Trifluoroacetic acid

HRID 2103351Notes

Reaction equation

HRID 2103351 reaction equation
[OH:1][C:2]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[CH2:7][CH2:6][CH:5]([NH:8][C@H:9]2[CH2:13][CH2:12][N:11]([C:14](=[O:29])[CH2:15][NH:16][C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[CH2:10]2)[CH2:4][CH2:3]1.[CH2:36]=[O:37].[BH-](OC(C)=O)(OC(C)=O)[O:39][C:40](C)=O.[Na+]>C1COCC1>[OH:1][C:2]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[CH2:3][CH2:4][CH:5]([N:8]([CH3:40])[C@H:9]2[CH2:13][CH2:12][N:11]([C:14](=[O:29])[CH2:15][NH:16][C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[CH:19]=3)[CH2:10]2)[CH2:6][CH2:7]1.[C:36]([OH:39])([C:24]([F:27])([F:26])[F:25])=[O:37]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11409228HCID 11409228, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 11318085HCID 11318085, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-{(3S)-3-[(4-hydroxy-4-pyridin-2-ylcyclohexyl)amino]pyrrolidin-1-yl}-2-oxoethyl)-3-(trifluoromethyl)benzamide (49 mg, 0.1 mmol) and formaldehyde (0.3 mL, 37% water solution) in THF (2 mL) was added Na(OAc)3BH (64 mg, 0.3 mmol). After being stirred at room temperature overnight, the reaction was quenched by addition of a saturated NaHCO3 solution. The resulting solution was extracted with EtOAc and the EtOAc layer was dried (MgSO4) and concentrated. Purification by prep HPLC provided the title compound as a TFA salt. MS (M+H)+ 505.

Workup

  1. customthe reaction was quenched by addition of a saturated NaHCO3 solution
  2. extractionThe resulting solution was extracted with EtOAc
  3. dry with materialthe EtOAc layer was dried (MgSO4)
  4. concentrationconcentrated
  5. customPurification by prep HPLC

Sources & evidence

ORD record
ord-724c2c3033cb47b4962f3fab5e14056d
Source dataset
uspto-grants-2009_08
Patent number
US07576089B2

Reaction notes

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