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

HRID 1747489Notes

Reaction equation

HRID 1747489 reaction equation
C([O:3][C:4](=[O:32])[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:28]3[S:27][C:26](=[O:29])[NH:25][C:24]=3[CH:23]=[C:22]([Br:30])[CH:21]=2)[C:11]1=[O:31])[CH2:7][CH2:8][CH3:9])C.[Li+].[OH-].Cl>O1CCOCC1.O>[Br:30][C:22]1[CH:21]=[C:20]([CH2:19][N:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]([C@@H:6]([CH2:7][CH2:8][CH3:9])[CH2:5][C:4]([OH:32])=[O:3])[C:11]2=[O:31])[C:28]2[S:27][C:26](=[O:29])[NH:25][C:24]=2[CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 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 ester

Product 1

HCID 59497458(S)-3-[3-(5-Bromo-2-oxo-2,3-dihydro-benzothiazol-7-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acidYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

(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 (33 mg, 0.06 mmol) is dissolved in dioxane (3 mL) and then LiOH (8 mg, 0.3 mmol) in water (3 mL) is added to the reaction. The reaction is stirred for 1 hour then acidified with 4N HCl and the solvents evaporated in vacuo. The resulting crude solid is purified on reverse phase LC/MS to give 10 mg (32%) of the title compound as a white solid. LCMS (ESMS): m/z 491.8 (M+H+).

Workup

  1. customthe solvents evaporated in vacuo
  2. customThe resulting crude solid is purified on reverse phase LC/MS

Sources & evidence

ORD record
ord-46d8b2062c384a33bcd371902b4278f6
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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