Potassium Hydroxide → HCID 68292087, compound

HRID 1507983Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH3:20])[C:13]([CH3:19])([CH3:18])[C:14]([O:16]C)=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH3:20])[C:13]([CH3:19])([CH3:18])[C:14]([OH:16])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of (R)-methyl 3-(((benzyloxy)carbonyl)amino)-2,2-dimethylbutanoate (2.2 g, 7.88 mmol) in methanol (25 mL) was KOH (3.54 g, 63.0 mmol) solution and stirred at 65° C. for overnight. Reaction mass was concentrated under reduced pressure to remove methanol. The residue was diluted with water (50 mL) and acidified to pH 5 using 1.5N HCl solution and extracted with ethyl acetate (2×200 mL), the combined organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to yield (R)-3-(((benzyloxy) carbonyl)amino)-2,2-dimethylbutanoic acid (1.2 g, 56.9%) as colorless oil. 1HNMR (400 MHz, DMSO-d6) δ ppm: 12.23 (bs, 1H), 7.30-7.39 (m, 5H), 5.03 (s, 2H), 3.92-3.98 (m, 1H), 0.98-1.09 (m, 9H). LCMS conditions: Column: Ascentis C18 (5×2.1 mm-2.7 μm); Mobile Phase A: 2% ACN-98% H2O-10 mM NH4COOH; Mobile Phase B: 98% CAN-2% H2O-10 mM NH4COOH, Flow: 1.0 mL/min, Retention Time: 1.639 min, Purity: 86.5% (m/z=266.2 M+).

Workup

customReaction mass
concentrationwas concentrated under reduced pressure
customto remove methanol
additionThe residue was diluted with water (50 mL)
extractionextracted with ethyl acetate (2×200 mL)
dry with materialthe combined organic layer was dried over anhydrous sodium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-a0296ed2269f43dc806507954ee09cdc
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221826B2

Reaction notes

Loading…