(6R, 7S)-2,2-dimethyl-7-(1-methoxy-1-methylethyl)-1-aza-3-oxabicyclo[4.2.0]octan-8-one → (3S, 4R)-4-(2-hydroxyethyl)-3-(1-methoxy-1-methylethyl)azetidin-2-one

HRID 235754Notes

Reaction equation

CC1(C)[O:9][CH2:8][CH2:7][C@H:6]2[N:3]1[C:4](=[O:15])[C@@H:5]2[C:10]([O:13][CH3:14])([CH3:12])[CH3:11]>C(O)(=O)C.O>[OH:9][CH2:8][CH2:7][C@H:6]1[NH:3][C:4](=[O:15])[C@@H:5]1[C:10]([O:13][CH3:14])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of (6R, 7S)-2,2-dimethyl-7-(1-methoxy-1-methylethyl)-1-aza-3-oxabicyclo[4.2.0]octan-8-one (142.3 mg) in a mixture of acetic acid (2.28 ml) and water (0.57 ml) was heated at 65° C. for 1.5 hours. The mixture was cooled to ambient temperature and then evaporated in vacuo. Xylene was added to the residue and the resultant suspension was evaporated in vacuo. The residue was dissolved in a mixture of methanol and xylene, and the resultant solution was evaporated in vacuo. This operation was repeated once and the residue was chromatographed on silica gel (1.5 g) eluting with a mixture of methylene chloride and acetone (10:1 to 1:1) to give (3S, 4R)-4-(2-hydroxyethyl)-3-(1-methoxy-1-methylethyl)azetidin-2-one (111.3 mg).

Workup

temperatureThe mixture was cooled to ambient temperature
customevaporated in vacuo
additionXylene was added to the residue
customthe resultant suspension was evaporated in vacuo
dissolutionThe residue was dissolved in a mixture of methanol and xylene
customthe resultant solution was evaporated in vacuo
customthe residue was chromatographed on silica gel (1.5 g)
washeluting with a mixture of methylene chloride and acetone (10:1 to 1:1)

Sources & evidence

ORD record: ord-1fc8670a0d31472081fb55a151a34e4a
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04640915

Reaction notes

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