Trifluoroacetic acid → HCID 57973826, compound

HRID 1864802Notes

Reaction equation

HRID 1864802 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:58]=[CH:57][C:12]([CH2:13][N:14]([CH2:22][C:23]2[O:27][CH:26]=[C:25]([C:28]3[CH:56]=[CH:55][C:31]4[N:32](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[C:33](=[O:35])[O:34][C:30]=4[CH:29]=3)[CH:24]=2)[CH:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1>ClCCl>[F:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]([CH2:22][C:23]2[O:27][CH:26]=[C:25]([C:28]3[CH:56]=[CH:55][C:31]4[NH:32][C:33](=[O:35])[O:34][C:30]=4[CH:29]=3)[CH:24]=2)[CH:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[CH:57][CH:58]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68751446HCID 68751446, compound

Product 1

HCID 57973826HCID 57973826, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 mL of 95% aqueous TFA was added to a solution of 6-(5-{[(4-fluoro-benzyl)-(1-methyl-piperidin-4-yl)-amino]-methyl}-furan-3-yl)-3-trityl-3H-benzooxazol-2-one (64 mg, 0.09 mmol) in 2 mL of dichloromethane, and the resulting mixture was stirred at room temperature for 1 h. The solvent was removed to afford the crude product. Purification was achieved via flash silica gel chromatography (elution with DCM:MeOH:AcOH:water). The pooled fractions were combined and the solvent was removed in vacuo with co-evaporation of residual AcOH using toluene to give 16 mg of product. LC/MS (long run): Retention time, 3.83 min; (M+H)=436.

Workup

  1. customThe solvent was removed
  2. customto afford the crude product
  3. customPurification
  4. washwas achieved via flash silica gel chromatography (elution with DCM:MeOH:AcOH:water)
  5. customthe solvent was removed in vacuo with co-evaporation of residual AcOH

Sources & evidence

ORD record
ord-aedf0dbd042b46b9ba79e4c0b4fea9c8
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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