Ethyl Acetate → HCID 86600749, compound

HRID 2252447Notes

Reaction equation

HRID 2252447 reaction equation
[CH3:1][O:2][P:3]([C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C@@H:19]3[C@@H:22]([CH2:23][CH2:24][C@H:25]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[C:21](=[O:41])[N:20]3[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[C:15]([O:48][Si](C(C)(C)C)(C)C)[CH:14]=2)[CH:10]=[CH:11][CH:12]=1)(=[O:6])[O:4][CH3:5].[F-].[K+].C(OCC)(=O)C>CO>[CH3:1][O:2][P:3]([C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C@@H:19]3[C@@H:22]([CH2:23][CH2:24][C@H:25]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[C:21](=[O:41])[N:20]3[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[C:15]([OH:48])[CH:14]=2)[CH:10]=[CH:11][CH:12]=1)(=[O:6])[O:4][CH3:5]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 522689Potassium FluorideHCID 86600748HCID 86600748, compound

Product 1

HCID 86600749HCID 86600749, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethyl(3′-{[tert-butyl(dimethyl)silyl]oxy}-4′-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}biphenyl-3-yl)phosphonate (0.047 g, 0.058 mmol) was stirred at room temperature in dry methanol (2 mL) under a nitrogen atmosphere. Potassium fluoride (0.02 g, 0.34 mmol) was added and the reaction mixture was stirred for 30 min at room temperature. The solution was poured into ethyl acetate and washed successively with water (2×), and brine. The organic solution was dried over sodium sulfate, filtered and the solvent was removed by rotary evaporation under reduced pressure. Dimethyl(4′-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}-3′-hydroxybiphenyl-3-yl)phosphonate was obtained as a colorless glass (0.041 g, 100%) was used directly in the next reaction without further purification; MS [M−H]+ 688

Workup

  1. washwashed successively with water (2×), and brine
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed by rotary evaporation under reduced pressure

Sources & evidence

ORD record
ord-092b2f4b1b14477094e9f992d46affd6
Source dataset
uspto-grants-2008_01
Patent number
US07320972B2

Reaction notes

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