beta-[[(1,1-Dimethylethoxy)carbonyl]amino]-alpha-hydroxycyclohexanebutanoic acid, 1-methylethyl ester → beta-Amino-alpha-hydroxycyclohexanebutanoic acid, 1-methylethyl ester

HRID 846466Notes

Reaction equation

CC(C)(OC([NH:7][CH:8]([CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH:9]([OH:16])[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])=O)C>C(Cl)Cl>[NH2:7][CH:8]([CH2:17][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)[CH:9]([OH:16])[C:10]([O:12][CH:13]([CH3:14])[CH3:15])=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

β-[[(1,1-dimethylethoxy)carbonyl]amino]-α-hydroxycyclohexanebutanoic acid, 1-methylethyl ester (mixture of [R-(R*,S*)] and [S-(R*,R*)]isomers) (Example F), 3.4 g (10 mmol), is dissolved in methylene chloride, cooled to 0° C. and hydrochloric acid gas is bubbled in for five minutes every 15 minutes for two hours. The solution is diluted with ethyl acetate (50 ml) washed with saturated sodium bicarbonate solution (100 ml) and then with saturated brine solution (100 ml). The organics are separated, dried over magnesium sulfate and evaporated to dryness in vacuo to give 1.75 g (73%) of the title compound as an oil.

Workup

customhydrochloric acid gas is bubbled in for five minutes every 15 minutes for two hours
additionThe solution is diluted with ethyl acetate (50 ml)
washwashed with saturated sodium bicarbonate solution (100 ml)
customThe organics are separated
dry with materialdried over magnesium sulfate
customevaporated to dryness in vacuo

Sources & evidence

ORD record: ord-c0c0271fc7a84572b584da7e38f4868b
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05135914

Reaction notes

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