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Cyanogen Bromide → HCID 9995821、化合物

HRID 1683938
ノート
印刷プレビュー

反応式

HRID 1683938 の反応式
[C:1]([NH:4][C@H:5]1[C@H:13]([C@@H:14]([C@@H:16]([CH2:18][OH:19])[OH:17])[OH:15])[O:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C@@H:6]1[NH2:20])(=[O:3])[CH3:2].C([O-])(=O)C.[Na+].[N:26]#[C:27]Br>CO>[C:1]([NH:4][C@H:5]1[C@H:13]([C@@H:14]([C@@H:16]([CH2:18][OH:19])[OH:17])[OH:15])[O:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C@@H:6]1[NH:20][C:27]#[N:26])(=[O:3])[CH3:2]
参加物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 10476Cyanogen BromideHCID 4455334-amino-2-deoxy-2,3-didehydro-N-acetylneuraminic acidHCID 517045Sodium Acetate

生成物 1

HCID 9995821HCID 9995821、化合物収率 106.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

5-(Acetylamino)-4-amino-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid (3 g, 10.35 mmol) was suspended in methanol (37.5 ml) and sodium acetate (1.89 g, 23.1 mmol) was added, causing a "caking" of the suspension and making stirring difficult. To this at 21° C. with exclusion of moisture was added a solution of cyanogen bromide (1.14 g, 10.8 mmol) in methanol (150 ml), in a dropwise manner. Stirring gradually became easier, until a readily stirrable suspension was obtained. Addition was complete in 3.5 hr. The mixture was then stirred at 21° C. with exclusion of moisture for 44 hr. The small amount of remaining solid was filtered off and solvent evaporated in vacuo to an orange-brown foam. The foam was taken up in methanol (125 ml) and with rapid stirring at 21° C. was treated dropwise with propan-2-ol (130 ml). The precipitate was filtered off, washed with iPrOH:MeOH 3:2, and combined filtrate and washings evaporated to give the title compound as a pale yellow foam (3.48 g).

後処理

  1. stirringStirring gradually
  2. customwas obtained
  3. additionAddition
  4. stirringThe mixture was then stirred at 21° C. with exclusion of moisture for 44 hr
  5. filtrationwas filtered off
  6. customsolvent evaporated in vacuo to an orange-brown foam
  7. stirringwith rapid stirring at 21° C.
  8. additionwas treated dropwise with propan-2-ol (130 ml)
  9. filtrationThe precipitate was filtered off
  10. washwashed with iPrOH:MeOH 3:2
  11. customevaporated

出典と根拠

ORDレコード
ord-1bd2d4b451024932bb3c36f34d0cd157
出典データセット
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05639786

反応ノート

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