Hydrochloric Acid → (R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic acid

HRID 1908963Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:15][C:16]1[CH:21]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:17]=1[F:24])[CH2:10][C:11]([O:13]C)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.[OH-].[Li+].Cl>O.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:15][C:16]1[CH:21]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:17]=1[F:24])[CH2:10][C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

53 mg of (R)-methyl 3-(t-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoate, 1.5 mL of tetrahydrofuran, and 0.5 mL of water were added to 25 mL flask and the resulting reaction solution was cooled to 0° C. 7.32 mg of lithium hydroxide was added to the reaction solution and stirred for 6 hours while the reaction temperature was naturally increased to room temperature. After completing the reaction, 5 mL of ethyl acetate and 5 mL of water were added to the reaction solution and stirred for 10 minutes. An aqueous layer was isolated, cooled at 0° C., and 2 N hydrochloric acid aqueous solution was dropped to adjust to pH 3-4. The aqueous layer was extracted with methylene chloride:methanol=10:1 solvent, dehydrated with magnesium sulfate, and then concentrated under reduced pressure to obtain 40.8 mg of a title compound.

Workup

customthe resulting reaction solution
temperaturewas naturally increased to room temperature
additionwere added to the reaction solution
stirringstirred for 10 minutes
customAn aqueous layer was isolated
temperaturecooled at 0° C.
extractionThe aqueous layer was extracted with methylene chloride
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-47acc04cff214a72b27826c27f1c438b
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598347B2

Reaction notes

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