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Trifluoroacetic acid → Benzyl 6-(2-hydroxy-2-propyl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate

HRID 1388285
ノート
印刷プレビュー

反応式

HRID 1388285 の反応式
[CH2:1]([CH:4]1[N:7]([C:8]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:6](=[O:38])[CH:5]1[C:39]([OH:42])([CH3:41])[CH3:40])[CH:2]=C.FC(F)(F)C(O)=O.O=[O+][O-]>C(OCC)(=O)C>[OH:42][C:39]([CH:5]1[C:6](=[O:38])[N:7]2[CH:4]1[CH2:1][CH:2]=[C:8]2[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])([CH3:41])[CH3:40]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 24823OzoneHCID 12800412HCID 12800412、化合物

生成物 1

HCID 12796946Benzyl 6-(2-hydroxy-2-propyl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

The cis-isomer of 4-allyl-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)-3-(2-hydroxy-2-propyl)azetidin-2-one (10 ) (0.188 g) was dissolved in ethyl acetate (14 ml). An excess of trifluoroacetic acid (0.37 g) was added and the mixture cooled to -78° C. Ozone was passed into the reaction mixture until it was pale blue in colour. Argon was then bubbled through the solution until all the excess ozone had been removed. A solution of triphenylphosphine (0.085 g) in ethyl acetate was added and argon bubbled through the mixture for a further ten minutes. The reaction flask was then transferred to an ice bath and a saturated aqueous solution of sodium bicarbonate (20 ml) was added and the mixture stirred vigourously under argon for thirty minutes. The ethyl acetate layer was separated, washed with brine and dried.

後処理

  1. customArgon was then bubbled through the solution until all the excess ozone
  2. customhad been removed
  3. additionA solution of triphenylphosphine (0.085 g) in ethyl acetate was added
  4. customargon bubbled through the mixture for a further ten minutes
  5. customThe reaction flask was then transferred to an ice bath
  6. additiona saturated aqueous solution of sodium bicarbonate (20 ml) was added
  7. customThe ethyl acetate layer was separated
  8. washwashed with brine
  9. customdried

出典と根拠

ORDレコード
ord-d29ec7f582c74a858a11cf9014f23279
出典データセット
uspto-grants-1984_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04431587

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート