Hydrochloric Acid → (1R,3S,5R)-2-Aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester hydrochloride

HRID 1052126Notes

Reaction equation

HRID 1052126 reaction equation
C(OC([N:8]1[C@H:13]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=O)(C)(C)C.[ClH:24]>O1CCOCC1>[ClH:24].[CH2:17]([O:16][C:14]([C@@H:13]1[CH2:12][C@@H:11]2[C@@H:9]([CH2:10]2)[NH:8]1)=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68283955(1R,3S,5R)-2-Aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 3-benzyl ester 2-tert-butyl ester

Product 1

HCID 90020119(1R,3S,5R)-2-Aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (1R,3S,5R)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 3-benzyl ester 2-tert-butyl ester (2.69 g, 8.48 mmol) in dioxane was added HCl (4N in dioxane, 10.6 mL, 42.4 mmol). The reaction mixture was stirred at RT overnight and subsequently lyophilized. MS (LC/MS): 218 [M+H]+.

Sources & evidence

ORD record
ord-7fb6556ea5b347308af4419dd92b0ec9
Source dataset
uspto-grants-2016_07
Patent number
US09388199B2

Reaction notes

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