Trifluoroacetic acid → (2-Amino-1,3-benzothiazol-6-yl) 4-[(2-hydroxy-2-methylpropyl)amino]benzenesulfonate;2,2,2-trifluoroacetic acid

HRID 1867996Notes

Reaction equation

HRID 1867996 reaction equation
C(OC([NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([O:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([NH:28][CH2:29][C:30]([OH:33])([CH3:32])[CH3:31])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1)=O)(C)(C)C.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>ClCCl.O>[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].[NH2:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([O:18][S:19]([C:22]3[CH:23]=[CH:24][C:25]([NH:28][CH2:29][C:30]([OH:33])([CH3:31])[CH3:32])=[CH:26][CH:27]=3)(=[O:20])=[O:21])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 579808624-(2-Hydroxy-2-methylpropylamino)benzenesulfonic acid 2-tert-butoxycarbonylaminobenzothiazol-6-yl ester2×

Product 1

HCID 86612154(2-Amino-1,3-benzothiazol-6-yl) 4-[(2-hydroxy-2-methylpropyl)amino]benzenesulfonate;2,2,2-trifluoroacetic acidYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2-hydroxy-2-methylpropylamino)benzenesulfonic acid 2-tert-butoxycarbonylaminobenzothiazol-6-yl ester (intermediate 81) (170 mg, 0.344 mmol) and trifluoroacetic acid (14.9 g, 130.7 mmol) in 10 ml of dichloromethane and 100 μl of water is stirred for 2 hours at room temperature. The reaction medium is evaporated to dryness, taken up in ethyl acetate and washed with water, and then with saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated to dryness to give 130 mg of 4-(2-hydroxy-2-methylpropylamino)benzenesulfonic acid 2-aminobenzothiazol-6-yl ester; compound with trifluoroacetic acid in a yield of 96%.

Workup

  1. customThe reaction medium is evaporated to dryness
  2. washwashed with water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-956bc62633a94c44b76272b7e5d65f00
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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