Trifluoroacetic acid → HCID 60164866, compound

HRID 1976429Notes

Reaction equation

HRID 1976429 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:11])=[O:10])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=[O:13]>>[OH:13][NH:11][C:9](=[O:10])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86986(4-Hydroxyphenyl)acetamide

Product 1

HCID 60164866HCID 60164866, compound

Procedure

A 450 mg (1.007 mmol) portion of ′N-(tert-butoxy)-2-({[4-2-butynyloxy)phenyl]sulfonyl}amino)-2-(4-hydroxyphenyl)acetamide was stirred in neat TFA at room temperature for 72 h. TFA was removed in vacuo. The residue was chromatographed on preparative TLC, eluting with 1% HOAc and 10% MeOH in dichloromethane to provide 33.8 mg (9%) of 2-{[4-(2-butynyloxy)phenyl]-sulfonyl}amino)-N-hydroxy-2-(4-hydroxyphenyl)acetamide as a white solid. Electrospray Mass Spec 391.4 (M+H)+

Workup

  1. customTFA was removed in vacuo
  2. customThe residue was chromatographed on preparative TLC
  3. washeluting with 1% HOAc and 10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-f078036408f44854af85539191f1e467
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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