Hydrochloric Acid → 1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-ethoxycarbonylmethylthio-8-carboxymethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine

HRID 458927Notes

Reaction equation

HRID 458927 reaction equation
[O:1]=[S:2]1(=[O:31])[C:8]2[CH:9]=[C:10]([O:14][CH2:15][C:16]([OH:18])=[O:17])[C:11](Br)=[CH:12][C:7]=2[N:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:5][C:4]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:25][CH3:26])[CH2:3]1.C([O-])([O-])=O.[Cs+].[Cs+].[C:38]([O:42][CH2:43][CH3:44])(=[O:41])[CH2:39][SH:40].Cl>O.CN(C=O)C>[O:1]=[S:2]1(=[O:31])[C:8]2[CH:9]=[C:10]([O:14][CH2:15][C:16]([OH:18])=[O:17])[C:11]([S:40][CH2:39][C:38]([O:42][CH2:43][CH3:44])=[O:41])=[CH:12][C:7]=2[N:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:5][C:4]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:25][CH3:26])[CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 12185Ethyl ThioglycolateHCID 223931311,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-carboxymethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine

Product 1

HCID 184424711,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-ethoxycarbonylmethylthio-8-carboxymethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepineYield 100.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-carboxymethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 9; 50 mg, 0.098 mmol) and Cs2CO3 (51 mg, 0.15 mmol) were added to DMF (2.0 ml) and ethyl thioglycolate (0.02 ml, 0.15 mmol) was added. The reaction mixture was subjected to microwave irradiation in a Smith Synthesiser at 150° C. for 5 min. The reaction mixture was diluted with water (100 ml), made acidic with HCl (1 M), extracted with DCM (3×10 ml) and the collected organic layers were dried (MgSO4) to give the crude title compound (54 mg). M/z 550.2.

Workup

  1. additionwas added
  2. customirradiation in a Smith Synthesiser at 150° C. for 5 min
  3. extractionextracted with DCM (3×10 ml)
  4. dry with materialthe collected organic layers were dried (MgSO4)

Sources & evidence

ORD record
ord-c6c3cb481ac0444cad8c4bcd2ffa9731
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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