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Dimethyl Sulfoxide → tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-formyl-1,4-oxazepane-4-carboxylate

HRID 1022647
ノート
印刷プレビュー

反応式

HRID 1022647 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:13]=[C:14]([C@H:19]2[C@H:25]([CH2:26][OH:27])[O:24][CH2:23][CH2:22][N:21]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:20]2)[CH:15]=[CH:16][C:17]=1[Cl:18].O>C1COCC1.C(N(CC)CC)C>[Cl:11][C:12]1[CH:13]=[C:14]([C@H:19]2[C@H:25]([CH:26]=[O:27])[O:24][CH2:23][CH2:22][N:21]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:20]2)[CH:15]=[CH:16][C:17]=1[Cl:18]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 65578Oxalyl chlorideHCID 66975324tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-(hydroxymethyl)-1,4-oxazepane-4-carboxylate

生成物 1

HCID 86663857tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-formyl-1,4-oxazepane-4-carboxylate収率 96.9%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
2 回
HCID 8471Triethylamine溶媒

実験手順

To a solution of oxalyl chloride (1.52 g) in THF (20 mL) was added dimethyl sulfoxide (1.87 g) at −78° C., and the mixture was stirred for 20 min. A solution of tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (3.0 g) in THF (10 mL) and triethylamine (7.78 mL) were added at −78° C., and the mixture was warmed to room temperature and stirred for 1 hr. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-50%)) to give the title compound (2.89 g) as a colorless solid.

後処理

  1. stirringstirred for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-50%))

出典と根拠

ORDレコード
ord-eae05214f4074e90ab220ec57e287eb7
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08722662B2

反応ノート

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