HCID 18104467, compound → HCID 22881832, compound

HRID 1765977Notes

Reaction equation

C[O:2][C:3](=O)[C@H:4]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:5][C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].[H-].C([Al+]CC(C)C)C(C)C>COCCOC.C1(C)C=CC=CC=1>[CH:8]1([C:6]([NH:5][C@H:4]([CH:3]=[O:2])[CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:7])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

Conditions

Temperature: 70 °C

Procedure

N-Cyclohexanoylphenylalanine methyl ester (0.5 g) is dissolved in ethylene glycol dimethyl ether (20 mL). The solution is cooled to 70° C. and diisobutylaluminum hydride (2.04 mL of a 1.5M solution in toluene) is added. The resulting reaction mixture is stirred at −70° C. for 2 hours. The reaction is quenched by dropwise addition of 2N hydrochloric acid. The mixture is extracted with cold ethyl acetate. The ethyl acetate solution is washed with brine and dried over sodium sulfate. Concentration in vacuo furnishes a white solid, which is purified by silica gel chromatography. 1H NMR (300 MHz, DMSO-d6): 9.5 (s, 1H), 8.2 (d, 1H), 7.2 (m, 5H), 4.2 (m, 1H), 3.2 (d, 1H), 2.7 (d, 1H), 2.1 (m, 1H), 1.6 (br.m, 4H), 1.2 (br.m, 6H). R (KBr): 3300, 3050, 2900, 2850, 2800, 1700, 1600, 1500 cm−1.

Workup

customThe resulting reaction mixture
customThe reaction is quenched by dropwise addition of 2N hydrochloric acid
extractionThe mixture is extracted with cold ethyl acetate
washThe ethyl acetate solution is washed with brine
dry with materialdried over sodium sulfate
concentrationConcentration in vacuo
customfurnishes a white solid, which
customis purified by silica gel chromatography

Sources & evidence

ORD record: ord-a840cbb76c8c47b8b4233e47a5f7fcf8
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07229966B2

Reaction notes

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