Hydrochloric Acid → Benzyl N-[(3R,6S)-6-(hydroxymethyl)tetrahydropyran-3-YL]carbamate

HRID 470690ノート

反応式

HRID 470690 の反応式
ClC1N=C2NC(=O)[C@]3(C4(CCC(C)(C)CC4)[N:17]4[C@@H](C(=O)[O:14][C@@H:15](C5C=CC=CC=5)[C@H:16]4[C:26]4[CH:31]=[CH:30][CH:29]=CC=4)[C@@H]3C3C=CC=C(Cl)C=3F)C2=CC=1.[CH2:48]([O:55][C:56](Cl)=[O:57])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.Cl.[OH-:60].[Na+]>>[CH2:48]([O:55][C:56]([NH:17][C@@H:16]1[CH2:26][CH2:31][C@@H:30]([CH2:29][OH:60])[O:14][CH2:15]1)=[O:57])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 86672583(3'S,4'R,7'S,8'S,8a'R)-6''-chloro-8'-(3-chloro-2-fluorophenyl)-4,4-dimethyl-3',4'-diphenyl-3',4',8',8a'-tetrahydro-1'H-dispiro[cyclohexane-1,6'-pyrrolo[2,1-c][1,4]oxazine-7',3''-pyrrolo[2,3-b]pyridine]-1',2''(1''H)-dione

生成物 1

HCID 68310822Benzyl N-[(3R,6S)-6-(hydroxymethyl)tetrahydropyran-3-YL]carbamate収率 37%

実験手順

The compound (3.5 g, 21.0 mmol) obtained in Step 1 above was dissolved in 5N aqueous sodium hydroxide solution (40 ml) and benzyloxycarbonyl chloride (3.3 ml, 23.0 mmol) was added dropwise at 0° C. After stirring at room temperature for 16 hours, the reaction mixture was rendered acidic by addition of 1N hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, diethyl ether and hexane were added to the residue obtained and then the slurry was filtered and dried to give 2.06 g (37%) of the title compound as a colorless solid.

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure, diethyl ether and hexane
  5. additionwere added to the residue
  6. customobtained
  7. filtrationthe slurry was filtered
  8. customdried

出典と根拠

ORDレコード
ord-3289d86b870d43d98d74694a5ba4dae8
出典データセット
uspto-grants-2014_01
特許番号
US08629133B2

反応ノート

読み込み中…