Ammonium fluoride → (S)-4-Benzyl-3-(3-[2-hydroxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl]-(2S)-2-methoxy-propionyl)-oxazolidin-2-one

HRID 1394750Notes

Reaction equation

HRID 1394750 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:50])[C@@H:15]([O:48][CH3:49])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][C:26]2[N:27]=[C:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[O:29][C:30]=2[CH3:31])=[CH:19][C:18]=1[O:38][Si](C)(C)C(C)(C)C(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[F-]>CO.CCOC(C)=O>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:50])[C@@H:15]([O:48][CH3:49])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][C:26]2[N:27]=[C:28]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[O:29][C:30]=2[CH3:31])=[CH:19][C:18]=1[OH:38])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 25516Ammonium fluorideHCID 69283498(S)-4-Benzyl-3-(3-{2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-2-(2S)-methoxy-propionyl)-oxazolidin-2-one

Product 1

HCID 69280650(S)-4-Benzyl-3-(3-[2-hydroxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl]-(2S)-2-methoxy-propionyl)-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-4-benzyl-3-(3-{2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-2-(2S)-methoxy-propionyl)-oxazolidin-2-one (1.6 g, 2.29 mmol) in 10 ml methanol, was added NH4F (169 mg, 4.58 mmol) and the reaction mixture kept at r.t. for 2 hours. It was then diluted with AcOEt, washed with water/ice and brine, the aqueous layer was extracted with AcOEt, the combined organic layers dried over Na2SO4 and evaporated. The crude product (1.22 g) was found to be a mixture of the title compound and of (S)-3-{2-hydroxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methoxy-propionic acid methyl ester and used without purification for the last step.

Workup

  1. washwashed with water/ice and brine
  2. extractionthe aqueous layer was extracted with AcOEt
  3. dry with materialthe combined organic layers dried over Na2SO4
  4. customevaporated
  5. additiona mixture of the title compound
  6. customof (S)-3-{2-hydroxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methoxy-propionic acid methyl ester and used without purification for the last step

Sources & evidence

ORD record
ord-0291d518f3394337a3684a51e9dbbdd7
Source dataset
uspto-grants-2008_03
Patent number
US07348349B2

Reaction notes

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