Ethanol → (S)-3-[3-(5-Bromo-2-oxo-2,3-dihydro-benzothiazol-7-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester

HRID 1747488Notes

Reaction equation

HRID 1747488 reaction equation
[CH2:1]([O:3][C:4](=[O:37])[CH2:5][C@@H:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][C:20]2[CH:25]=[C:24]([Br:26])[CH:23]=[C:22]([N+:27]([O-])=O)[C:21]=2[S:30][C:31](=[O:35])N(C)C)[C:11]1=[O:36])[CH2:7][CH2:8][CH3:9])[CH3:2].C(O)C.[Sn](Cl)(Cl)(Cl)Cl>C(OC(=O)C)C>[CH2:1]([O:3][C:4](=[O:37])[CH2:5][C@@H:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][C:20]2[C:21]3[S:30][C:31](=[O:35])[NH:27][C:22]=3[CH:23]=[C:24]([Br:26])[CH:25]=2)[C:11]1=[O:36])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 24287Tin tetrachlorideHCID 59497582(S)-3-[3-(5-Bromo-2-dimethylcarbamoylsulfanyl-3-nitro-benzyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester

Product 1

HCID 59497273(S)-3-[3-(5-Bromo-2-oxo-2,3-dihydro-benzothiazol-7-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl esterYield 57.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

(S)-3-[3-(5-Bromo -2-dimethylcarbamoylsulfanyl-3-nitro-benzyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester (70 mg, 0.11 mmol) is suspended in ethylacetate (0.5 mL)/ethanol (0.5 mL) and then tin chloride (133 mg, 0.6 mmol) is added. The resulting suspension is equipped with a reflux condenser and heated to 75° C. for 1 hour. Upon completion the reaction is cooled to room temperature and the solvents evaporated in vacuo. The resulting solid is taken up in ethyl acetate and the product is filtered. The solvent is evaporated in vacuo and the resulting solid is purified via prep reverse phase LC to give 33 mg (54%) of the title compound. LCMS (ESMS): m/z 519.7 (M+H+).

Workup

  1. customThe resulting suspension is equipped with a reflux condenser
  2. temperatureUpon completion the reaction is cooled to room temperature
  3. customthe solvents evaporated in vacuo
  4. filtrationthe product is filtered
  5. customThe solvent is evaporated in vacuo
  6. customthe resulting solid is purified via prep reverse phase LC

Sources & evidence

ORD record
ord-5069da7b0bf048b58aeeccfefc152c8a
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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