Lithium hydroxide, monohydrate → 5-[[[5-Methoxy-3-(1-methylethoxy)benzo[b]thien2-yl]carbonyl]amino]pentanoic acid

HRID 1708214Notes

Reaction equation

HRID 1708214 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]2[S:7][C:8]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23]C)=[O:22])=[O:15])=[C:9]([O:10][CH:11]([CH3:13])[CH3:12])[C:5]=2[CH:4]=1.O[Li].O>CO.O>[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]2[S:7][C:8]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:15])=[C:9]([O:10][CH:11]([CH3:13])[CH3:12])[C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10643446Methyl 5-[[[5-methoxy-3-(1-methylethoxy)benzo[b]thien2-yl]carbonyl]amino]pentanoate

Product 1

HCID 105228645-[[[5-Methoxy-3-(1-methylethoxy)benzo[b]thien2-yl]carbonyl]amino]pentanoic acidYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 5-[[5-methoxy-3-(1-methylethoxy)benzo[b]thien-2-yl]carbonyl]aminovalerate (250 mg, 0.66 mmol) and 83 mg of LiOH-H2O in a mixture of 5 mL of methanol and 2 mL of water are stirred at room temperature for 7 hours. The reaction mixture is partitioned between ethyl acetate and aqueous HCl. The organic layer is washed with water, then brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Recrystallization from ethyl acetate:hexane gives 205 mg of product (85%); mp 135°-137° C.

Workup

  1. customThe reaction mixture is partitioned between ethyl acetate and aqueous HCl
  2. washThe organic layer is washed with water
  3. dry with materialbrine, dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-dc57ef9dc16444e1be0797846f4db037
Source dataset
uspto-grants-1994_10
Patent number
US05356926

Reaction notes

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