Diisopropylamine → 4-Fluorobenzenesulfonic acid 2-(2-methoxy-acetylamino)benzothiazol-6-yl ester

HRID 1867988Notes

Reaction equation

HRID 1867988 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][S:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:22][O:23][CH2:24][C:25](O)=[O:26].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(NC(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C.O>[CH3:22][O:23][CH2:24][C:25]([NH:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][S:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)(=[O:13])=[O:14])[CH:8]=[CH:7][C:5]=2[N:6]=1)=[O:26]

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 12251Methoxyacetic AcidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579808144-Fluorobenzenesulfonic acid 2-aminobenzothiazol-6-yl ester2×

Product 1

HCID 579808544-Fluorobenzenesulfonic acid 2-(2-methoxy-acetylamino)benzothiazol-6-yl esterYield 72%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-fluorobenzenesulfonic acid 2-aminobenzothiazol-6-yl ester (intermediate 16) (101.2 mg, 0.312 mmol), methoxyacetic acid (84.3 mg, 0.936 mmol), HBTU (355 mg, 0.936 mmol) and N,N-diisopropylamine (326 μl, 1.872 mmol) in 5 ml of dimethylformamide in a test tube, equipped with a magnetic bar, is stirred for 20 hours at room temperature. 100 ml of water are added and the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated. The residue obtained is taken up in ethyl acetate and purified on a Varian flash cartridge containing 5 g of silica of porosity 15-35μ, with a mixture of 1% methanol in dichloro-methane. After evaporating off the solvent, 89 mg of 4-fluorobenzenesulfonic acid 2-but-3-enoylaminobenzothiazol-6-yl ester are obtained (yellow oil) in a yield of 72%. LC/MS (method A1): [M+H]+: 397.11, retention time: 3.59 min.

Workup

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customevaporated
  4. customThe residue obtained
  5. custompurified on a Varian flash cartridge
  6. additioncontaining 5 g of silica of porosity 15-35μ
  7. additionwith a mixture of 1% methanol in dichloro-methane
  8. customAfter evaporating off the solvent, 89 mg of 4-fluorobenzenesulfonic acid 2-but-3-enoylaminobenzothiazol-6-yl ester
  9. customare obtained (yellow oil) in a yield of 72%

Sources & evidence

ORD record
ord-4feee44152e0407fb018768582c4aef1
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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