Hydrochloric Acid → HCID 11532128, compound

HRID 1173837Notes

Reaction equation

HRID 1173837 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:31]=[CH:30][C:13]3[S:14][C:15]([CH2:17][CH:18]4[CH2:22][CH2:21][N:20]([CH:23]5[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]5)[C:19]4=[O:29])=[CH:16][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1.O[Li].O.O1CCOCC1.Cl>O>[CH:23]1([N:20]2[CH2:21][CH2:22][CH:18]([CH2:17][C:15]3[S:14][C:13]4[CH:30]=[CH:31][C:10]([C:7]5[CH:8]=[CH:9][C:4]([C:3]([OH:32])=[O:2])=[CH:5][CH:6]=5)=[CH:11][C:12]=4[CH:16]=3)[C:19]2=[O:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrateHCID 59557397HCID 59557397, compound

Product 1

HCID 11532128HCID 11532128, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Heat a mixture of 4-[2-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-benzo[b]thiophen-5-yl]-benzoic acid methyl ester (250 mg, 0.64 mmol), LiOH.H2O (10 eq) into a dioxane (5 mL) and water (2 mL) at 80° C. for 1 hour. Add 2 M HCl (1 mL) and extract the mixture with ethyl acetate. Dry over sodium sulfate, filter, and concentrate. Purify by silica gel (20-50% ethyl acetate in hexanes) to give the title compound as a white powder (110 mg, 65%): MS (APCI-pos mode) m/z (rel intensity): 434.1 (M+H, 100%).

Workup

  1. temperatureHeat
  2. extractionextract the mixture with ethyl acetate
  3. dry with materialDry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify by silica gel (20-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-59d53fc8819a4941b757462759331680
Source dataset
uspto-grants-2010_11
Patent number
US07834194B2

Reaction notes

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