Potassium Hydroxide → 1-(1,1-Dimethylethyl) 2-[(3-carboxy-2-hydroxyphenoxy)methyl]-1-pyrrolidinecarboxylate

HRID 983794Notes

Reaction equation

CC1(C)[O:7][C:6]2[C:8]([O:12][CH2:13][CH:14]3[CH2:18][CH2:17][CH2:16][N:15]3[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:9][CH:10]=[CH:11][C:5]=2[C:4](=[O:26])C1.[OH-].[K+].[OH:30]S([O-])(=O)=O.[K+]>CS(C)=O>[C:22]([O:21][C:19]([N:15]1[CH2:16][CH2:17][CH2:18][CH:14]1[CH2:13][O:12][C:8]1[C:6]([OH:7])=[C:5]([CH:11]=[CH:10][CH:9]=1)[C:4]([OH:30])=[O:26])=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

Conditions

Temperature: 60 °C

Procedure

tert-butyl-2-(2, 2-dimethyl-4-oxo-4,4-benzo[1,3]dioxin-8-yloxymethyl)pyrrolidine-1-carboxylate 47 (1.65 g, 4.54 mmol) was dissolved in DMSO (9.5 mL) and then 49% aqueous KOH (1.5 mL) was added to the solution to form a basic reaction mixture. This basic reaction mixture was heated at 60° C. for 40 min. After cooling to room temperature and addition of 0.5 M aqueous KHSO4 (100 mL) gave an acidic suspension. The suspension was extracted with ether (4×250 mL) and the combined extracts were washed with brine (2×50 mL) and dried (Na2SO4). Evaporation of the ether gave 1.26 g (93%) of 3-(1-tert-butoxycarbonyl pyrrolidin-2-ylmethoxy)-2-hydroxy benzoic acid 48 as a brown solid.

Workup

customto form a basic reaction mixture
customThis basic reaction mixture
temperatureAfter cooling to room temperature
customgave an acidic suspension
extractionThe suspension was extracted with ether (4×250 mL)
washthe combined extracts were washed with brine (2×50 mL)
dry with materialdried (Na2SO4)
customEvaporation of the ether

Sources & evidence

ORD record: ord-da529edb0d1e40788497640236eaa377
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867200B1

Reaction notes

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