2-Chloro-3-[2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-5-oxazolyl]propionic acid → 3-[2-Methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-5-oxazolyl]propionic acid

HRID 350738Notes

Reaction equation

Cl[CH:2]([CH2:6][C:7]1[O:11][C:10]([CH3:12])=[N:9][C:8]=1[C:13]1[CH:22]=[CH:21][C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[CH:14]=1)[C:3]([OH:5])=[O:4]>C(O)(=O)C.[Zn]>[CH3:12][C:10]1[O:11][C:7]([CH2:6][CH2:2][C:3]([OH:5])=[O:4])=[C:8]([C:13]2[CH:22]=[CH:21][C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[CH:14]=2)[N:9]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2-chloro-3-[2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-5-oxazolyl]propionic acid (3.2 g) in acetic acid (30 mL) was added zinc powder (3.25 g) at 90° C. and the mixture was stirred at 90° C. for 15 min. The insoluble material was removed by filtration and the filtrate was concentrated. Water was added to the residue, and the precipitated crystals were collected by filtration and recrystallized from methanol to give 3-[2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-5-oxazolyl]propionic acid (2.25 g, yield 79%) as colorless prism crystals. melting point: 135–136° C.

Workup

customThe insoluble material was removed by filtration
concentrationthe filtrate was concentrated
additionWater was added to the residue
filtrationthe precipitated crystals were collected by filtration
customrecrystallized from methanol

Sources & evidence

ORD record: ord-f5dcf191f3644769b93e18c65b67f4ba
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183276B2

Reaction notes

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