Hexane → (S)-2-(benzoyloxy)-4-(benzyloxycarbonylamino)butanoic acid

HRID 1949611ノート

反応式

HRID 1949611 の反応式
C1[C@H](N)[C@@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2N)[C@H:4]([O:20][C@@H:21]2[O:25][C@H](CO)[C@@H](O[C@H]3O[C@@H](CN)[C@@H](O)[C@H](O)[C@H]3N)[C@H]2O)[C@@H:3](O)[C@@H:2]1[NH2:42].OS(O)(=O)=O.[C:48](=[O:51])([O-:50])[O-].[Na+].[Na+].Cl[C:55]([O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)=[O:56].C(=O)(O)[O-].[Na+].[CH3:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75]>O.O1CCCC1>[C:21]([O:20][C@@H:4]([CH2:3][CH2:2][NH:42][C:55]([O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)=[O:56])[C:48]([OH:50])=[O:51])(=[O:25])[C:72]1[CH:71]=[CH:70][CH:75]=[CH:74][CH:73]=1

参加物

8

反応物 5

HCID 8058HexaneHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 441375Paromomycin SulfateHCID 516892Sodium Bicarbonate

生成物 1

HCID 58503128(S)-2-(benzoyloxy)-4-(benzyloxycarbonylamino)butanoic acid収率 64.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirring solution of paromomycin sulfate (1, 76 g, 84 mmol) in water (209 mL) and tetrahydrofuran (1084 mL) at 0° C. was added a solution of sodium carbonate in water (254 mL, 218 mmol, 0.86 M), followed by the dropwise addition of benzyl chloroformate (120 mL, 840 mmol). Sodium bicarbonate (70.6 g, 840 mmol) was then added and the reaction was stirred for 3 hours. The two layers were separated and the organic layer was concentrated to a thick oil, which was diluted with ethyl acetate (400 mL) to give a total volume of 1.2 L. This was then dripped into hexane (9 L), and a precipitate formed. The filtrate was decanted off and concentrated to a white foam (2) (69.85 g, 64.5% yield).

後処理

  1. customThe two layers were separated
  2. concentrationthe organic layer was concentrated to a thick oil, which
  3. additionwas diluted with ethyl acetate (400 mL)
  4. customto give a total volume of 1.2 L
  5. customa precipitate formed
  6. customThe filtrate was decanted off

出典と根拠

ORDレコード
ord-06f479c264ea42a49a26854639c3c447
出典データセット
uspto-grants-2013_03
特許番号
US08399419B2

反応ノート

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