Diethyl Ether → N-[(5S)-3-(3-Fluoro-4-(4-hydroxymethylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-yl-methyl]acetamide

HRID 636708Notes

Reaction equation

HRID 636708 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:11]=[CH:12][N:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@H:24]([CH2:26][NH:27][C:28](=[O:30])[CH3:29])[O:23][C:22]3=[O:31])=[CH:17][C:16]=2[F:32])[CH:14]=1)(C(C)(C)C)(C)C.C(OCC)C>C(O)(=O)C.C1COCC1.O.ClCCl>[F:32][C:16]1[CH:17]=[C:18]([N:21]2[CH2:25][C@H:24]([CH2:26][NH:27][C:28](=[O:30])[CH3:29])[O:23][C:22]2=[O:31])[CH:19]=[CH:20][C:15]=1[N:13]1[CH:14]=[C:10]([CH2:9][OH:8])[N:11]=[CH:12]1

Participants

7

Reactant 2

HCID 3283Diethyl EtherHCID 10695375N-[(5S)-3-(4-(4-t-Butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-2-oxooxazolidin-5-ylmethyl]acetamide

Product 1

HCID 10760118N-[(5S)-3-(3-Fluoro-4-(4-hydroxymethylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-yl-methyl]acetamideYield 81.9%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-[(5S)-3-(4-(4-t-Butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-2-oxooxazolidin-5-ylmethyl]acetamide (6.0 g) was dissolved in a mixture of acetic acid (60 ml), THF (20 ml) and water (20 ml), and left to stir overnight at ambient temperature. Solvents were evporated at 40° in vacuo to give a gum. This was dissolved in dichloromethane (25 ml), and dry diethyl ether (100 ml) stirred in. The precipitate was triturated and stirred until properly solid, then filtered, washed with ether, and dried in vacuo to give product (3.7 g).

Workup

  1. waitleft
  2. customwere evporated at 40° in vacuo
  3. customto give a gum
  4. customThe precipitate was triturated
  5. stirringstirred until properly solid
  6. filtrationfiltered
  7. washwashed with ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-ecd986a4b0874fd29151c537ace5d614
Source dataset
uspto-grants-2001_02
Patent number
US06194441B1

Reaction notes

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