HCID 22644900, compound → HCID 9845460, compound

HRID 1976430Notes

Reaction equation

HRID 1976430 reaction equation
C([O:5][NH:6][C:7](=[O:34])[CH:8]([NH:19][S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]#[C:32][CH3:33])=[CH:25][CH:24]=1)(=[O:22])=[O:21])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]#[CH:18])=[CH:11][CH:10]=1)(C)(C)C>C(O)(C(F)(F)F)=O>[CH2:30]([O:29][C:26]1[CH:25]=[CH:24][C:23]([S:20]([NH:19][CH:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]#[CH:18])=[CH:11][CH:10]=2)[C:7]([NH:6][OH:5])=[O:34])(=[O:22])=[O:21])=[CH:28][CH:27]=1)[C:31]#[C:32][CH3:33]

Participants

3

Reactant 1

HCID 22644900HCID 22644900, compound

Product 1

HCID 9845460HCID 9845460, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

The 75 mg (0.154 mmol) sample of ′N-(tert-butoxy)-2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-2-[4-(2-propynyloxy)phenyl]acetamide was stirred in neat TFA at room temperature for 72 h TFA was removed in vacuo. The residue was chromatographed on prep. TLC eluting with 1% HOAc in 10% MeOH/CH2Cl2 to provide 11.1 mg (17%) of 2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-N-hydroxy-2-[4-(2-propynyloxy)phenyl]acetamide as a white solid was obtained. High Resolution Mass Spec 429.11155 (M+H)+;

Workup

  1. customwas removed in vacuo
  2. customThe residue was chromatographed on prep

Sources & evidence

ORD record
ord-300ff5578c3244ae842195c3614c7dc5
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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