Hydrochloric Acid → Methyl 2-((3R,5R,6S)-1-((S)-1-aminobutan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-3-yl)acetate

HRID 1048451Notes

Reaction equation

HRID 1048451 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[CH2:9][C@@H:10]([N:13]1[C@H:18]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[C@@H:17]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=2)[CH2:16][C@@:15]([CH2:34][C:35]([O:37][CH3:38])=[O:36])([CH3:33])[C:14]1=[O:39])[CH2:11][CH3:12])=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][CH2:9][C@@H:10]([N:13]1[C@H:18]([C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)[C@@H:17]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=2)[CH2:16][C@@:15]([CH2:34][C:35]([O:37][CH3:38])=[O:36])([CH3:33])[C:14]1=[O:39])[CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67999215Methyl 2-((3R,5R,6S)-1-((S)-1-(bis(tert-butoxycarbonyl)amino)butan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-3-yl)acetate

Product 1

HCID 58573400Methyl 2-((3R,5R,6S)-1-((S)-1-aminobutan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 2-((3R,5R,6S)-1-((S)-1-(bis(tert-butoxycarbonyl)amino)butan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-3-yl)acetate (167 mg, 0.246 mmol) prepared in Step A above in dioxane was stirred with HCl (4M, 0.6 mL) at rt for 2 h. Chromatography on silica gel (0 to 20% MeOH/DCM) gave the title compound. Mass Spectrum (ESI) m/z=477 (M+1).

Sources & evidence

ORD record
ord-16315e296cb1480e9373f529de24794e
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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