Diethyl Ether → HCID 57295923, compound

HRID 861888Notes

Reaction equation

HRID 861888 reaction equation
[NH2:1][C@H:2]1[C@@H:5]([C@@H:6]2[CH2:10][O:9][C:8]([CH3:12])([CH3:11])[O:7]2)[N:4]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C:3]1=[O:21].[C:22]1([CH2:28][C:29](Cl)=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.C(OCC)C>ClCCl>[CH3:11][C:8]1([CH3:12])[O:7][C@H:6]([C@H:5]2[N:4]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:3](=[O:21])[C@H:2]2[NH:1][C:29](=[O:30])[CH2:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:10][O:9]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 56989475HCID 56989475, compound

Product 1

HCID 57295923HCID 57295923, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of (3S,4S)-3-amino-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)azetidin-2-one (12.21 g, 41.8mmol) in dichloromethane (160 ml) was cooled to 0° C. and treated sequentially with phenylacetyl chloride (6.1 ml, 46.1 mmol), then triethylamine (6.4 ml, 45.9 mmol). After stirring at 0° C. for 15min., the mixture was warmed to room temperature and stirred for a further 30 min. The reaction mixture was diluted with dichloromethane and washed twice with water, then brine, The organic layer was dried over magnesium sulphate, filtered and the solvent evaporated in vacuo to yield a solid. Trituration with diethyl ether yielded the title compound (16.16 g, 94%) as a white amorphous solid; [α]D 0.0° (c=1.00 DMF); νmax (KBr) 1757, 1661 and 1510 cm- ; δH (CDCl3) 1.16 (3H, s), 1.25 (3H, s), 3.62 (2H, s), 3.69-3.82 (2H, m), 3.76 (3H, s), 4.02 (1H, m), 4.36 (1H, dd, J 5.5, 4.0 Hz), 5.58 (1H, dd, J 9.4, 5.5 Hz), 6.56 (1H, d, J 9.4 Hz), 6.83 (2H, d, J 8.9 Hz) and 7.25-7.40 (7H, m); m/z (EI) 410 (5); (CI, +ve ion, ammonia) 411 (MH+).

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. stirringstirred for a further 30 min
  3. washwashed twice with water
  4. dry with materialbrine, The organic layer was dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. customto yield a solid

Sources & evidence

ORD record
ord-51542ca25eac4d4090daf2d367e459b7
Source dataset
uspto-grants-1998_02
Patent number
US05716948

Reaction notes

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