HCID 22644754, compound → HCID 9865189, compound

HRID 2084890Notes

Reaction equation

HRID 2084890 reaction equation
C([O:5][NH:6][C:7](=[O:31])[CH:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]#[C:29][CH3:30])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)(C)(C)C>C(O)(C(F)(F)F)=O>[CH2:27]([O:26][C:23]1[CH:22]=[CH:21][C:20]([S:17]([NH:16][CH:8]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[C:7]([NH:6][OH:5])=[O:31])(=[O:19])=[O:18])=[CH:25][CH:24]=1)[C:28]#[C:29][CH3:30]

Participants

3

Reactant 1

HCID 22644754HCID 22644754, compound

Product 1

HCID 9865189HCID 9865189, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

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-acd750cf0857411bbafea70423d7c866
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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