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1,1-Dimethylethyl N-[(3S)-2,2-dimethyl-4-oxo-1-(phenylmethoxy)-3-azetidinyl]carbamate → (S)-tert-Butyl (1-hydroxy-2,2-dimethyl-4-oxoazetidin-3-yl)carbamate

HRID 1788788
Notes
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Reaction equation

HRID 1788788 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C:12]([CH3:14])([CH3:13])[N:11]([O:15]CC2C=CC=CC=2)[C:10]1=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C@H:9]1[C:12]([CH3:14])([CH3:13])[N:11]([OH:15])[C:10]1=[O:23])=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 140101021,1-Dimethylethyl N-[(3S)-2,2-dimethyl-4-oxo-1-(phenylmethoxy)-3-azetidinyl]carbamate

Product 1

HCID 14010104(S)-tert-Butyl (1-hydroxy-2,2-dimethyl-4-oxoazetidin-3-yl)carbamateYield 83.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl Acetate
Solvent

Procedure

A solution of 14.77 g (0.0461 mole) of (3S)-3-[(t-butyloxycarbonyl)amino]-4,4-dimethyl-1-(phenylmethoxy)-2-azetidinone in 15 ml of ethanol and 85 ml of ethyl acetate was hydrogenated over 0.75 g of 5% palladium-on-carbon catalyst for 1.5 hours at 1 atmosphere. The reaction mixture was filtered and concentrated to give a white solid. Recrystallization from ethyl acetate gave 8.82 g of the title compound, melting point 148°-149° C., [α]D =+31° (C =1, ethyl acetate).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customto give a white solid
  4. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-b8abfc5399164ec0b2d27d6533f14659
Source dataset
uspto-grants-1987_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04684722

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes