Hydrochloric Acid → HCID 22268688, compound

HRID 489121Notes

Reaction equation

HRID 489121 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][O:5][C:6]1[CH:14]=[C:13]2[CH2:15][CH2:16][CH2:17][C:12]2=[C:11]2[C:7]=1[C:8]([C:32](=[O:36])[C:33]([NH2:35])=[O:34])=[C:9]([CH3:31])[N:10]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[S:26][C:27]([Br:30])=[CH:28][CH:29]=1.[OH-].[Li+].Cl>O1CCOCC1.O>[NH2:35][C:33](=[O:34])[C:32]([C:8]1[C:7]2[C:11](=[C:12]3[CH2:17][CH2:16][CH2:15][C:13]3=[CH:14][C:6]=2[O:5][CH2:4][C:3]([OH:37])=[O:2])[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]2[S:26][C:27]([Br:30])=[CH:28][CH:29]=2)[C:9]=1[CH3:31])=[O:36]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 23405924HCID 23405924, compound

Product 1

HCID 22268688HCID 22268688, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-[2-(5-bromothiophen-2-yl)benzyl]-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic acid methyl ester (50 mg, 0.086 mmol) in dioxane (5 mL) was warmed until a clear solution was obtained. This solution was treated with 1M lithium hydroxide solution (1 mL) at room temperature for 90 min. The pH was adjusted to ˜3 with hydrochloric acid. The mixture was diluted with water and stirred for 15 min. The resulting precipitate was collected via vacuum filtration to provide 25 mg (51%) of the title compound as a green solid. TOS MS ES+ exact mass calculated for C27H24BrN2O5S (p+1): m/z=567.0589. Found: 567.0603.

Workup

  1. temperaturewas warmed until a clear solution
  2. customwas obtained
  3. filtrationThe resulting precipitate was collected via vacuum filtration

Sources & evidence

ORD record
ord-9ef147d33821404da5b6f1c8cd82a8bf
Source dataset
uspto-grants-2005_12
Patent number
US06974831B2

Reaction notes

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