Trifluoroacetic acid → HCID 9910408, compound

HRID 2414654Notes

Reaction equation

HRID 2414654 reaction equation
[OH:1][NH:2][C:3]([CH:5]1[C:10]([CH3:12])([CH3:11])[S:9][CH2:8][CH2:7][N:6]1[S:13]([C:16]1[CH:35]=[CH:34][C:19]([O:20][CH2:21][C:22]#[C:23][CH2:24][CH2:25][NH:26]C(=O)OC(C)(C)C)=[CH:18][CH:17]=1)(=[O:15])=[O:14])=[O:4].FC(F)(F)C(O)=O>ClCCl>[NH2:26][CH2:25][CH2:24][C:23]#[C:22][CH2:21][O:20][C:19]1[CH:34]=[CH:35][C:16]([S:13]([N:6]2[CH2:7][CH2:8][S:9][C:10]([CH3:12])([CH3:11])[CH:5]2[C:3]([NH:2][OH:1])=[O:4])(=[O:14])=[O:15])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 9849811HCID 9849811, compound

Product 1

HCID 9910408HCID 9910408, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.071 g (0.135 mmol) of tert-butyl 5-[4-({3-[(hydroxyamino)carbonyl]-2,2-dimethyl-4-thiomorpholinyl}sulfonyl)phenoxy]-3-pentynylcarbamate from Example 245, 1 mL of trifluoroacetic acid and 3 mL of dichloromethane was stirred for 1.5 h. The solution was concentrated in vacuo and the residue was triturated with ether to provide 0.058 g (79%) of 4-({4-[(5-amino-2-pentynyl)oxy]phenyl}sulfonyl)-N-hydroxy-2,2-dimethyl-3-thiomorpholine carboxamide as a pale orange solid. Electrospray Mass Spec: 428.3 (M+H)+

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-62d01091dad14dd6b422db2c7ac37097
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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