Hydrochloric Acid → HCID 22865764, compound

HRID 2258296Notes

Reaction equation

C([O:3][C:4](=O)[C@@H:5]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:6][C@H:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=1)[CH:8]([CH3:10])[CH3:9])C.CO.Cl>C1(C)C=CC=CC=1>[C:26]([O:25][C:23]([NH:22][C@@H:5]([CH2:6][C@H:7]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]([CH3:20])([CH3:19])[CH3:21])=[CH:16][CH:17]=1)[CH:8]([CH3:10])[CH3:9])[CH:4]=[O:3])=[O:24])([CH3:27])([CH3:28])[CH3:29]

Participants

Conditions

Temperature: -70 °C

Procedure

A 1.2M diisobutylal hydridesolution in toluene (4.2 ml) is slowly added dropwise at -75° C. to a solution of 2(S)-(tert-butoxycarbonyl)amino-4(S)-(p-tert-butyl-benzyl)-5-methyl-hexanoic acid ethyl ester (1 g) in toluene (20 ml). The reaction mixture is stirred for 30 minutes at -70° C., then 10 ml of methanol are added and the mixture is poured onto a mixture of ice and 1N hydrochloric acid (10 ml) and extracted with ethyl acetate. The title compound is obtained: Rf (dichloromethane)=0.35.

Workup

extractionextracted with ethyl acetate

Sources & evidence

ORD record: ord-ecc54b688b494b37879089e051b45957
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05659065

Reaction notes

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