(1R,2S,5S)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-benzyl ester 3-tert-butyl ester → (1R,2S,5S)-3-(tert-butoxycarbonyl)-6-oxa-3-azabicyclo[3.1.0]hexane-2-carboxylic acid
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]2[C@H:10]([O:11]2)[C@H:9]1[C:14]([O:16]CC1C=CC=CC=1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]2[C@H:10]([O:11]2)[C@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution (1R,2S,5S)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-benzyl ester 3-tert-butyl ester (2.62 g, 8.21 mmol) in ethyl acetate (32 mL) was hydrogenated under H2 with palladium hydroxide on carbon (1.15 g, 8.21 mmol) for 1 night. The reaction mixture was filtered over a glass fiber filter, quenched with Na2CO3 saturated aqueous solution and was extracted twice with EtOAc. The aqueous layer was acidified with HCl 1N to pH=2 and extracted 4 times with ethyl acetate, washed with brine, dried over Na2SO4, filtered and concentrated to give the desired material which was used in the next step without further purification. MS (UPLC): 230 [M+H]+, 228 [M−H]−.
Workup
- filtrationThe reaction mixture was filtered over a glass fiber
- filtrationfilter
- customquenched with Na2CO3 saturated aqueous solution
- extractionwas extracted twice with EtOAc
- extractionextracted 4 times with ethyl acetate
- washwashed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-101fc30ef59b4151b84b4beb1a08e381
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085555B2
Reaction notes
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