Triethylamine → 2-Deoxy-2-trifluoroacetamido-d-glucose

HRID 482126노트

반응식

HRID 482126 반응식
Cl.[OH:2][CH:3]1[O:11][C@H:10]([CH2:12][OH:13])[C@@H:8]([OH:9])[C@H:6]([OH:7])[C@H:4]1[NH2:5].C(N(CC)CC)C.[F:21][C:22]([F:29])([F:28])[C:23](OCC)=[O:24]>CO>[F:21][C:22]([F:29])([F:28])[C:23]([NH:5][C@@H:4]1[C@@H:6]([OH:7])[C@H:8]([OH:9])[C@@H:10]([CH2:12][OH:13])[O:11][CH:3]1[OH:2])=[O:24]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 2723635(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride

생성물 1

HCID 27607002-Deoxy-2-trifluoroacetamido-d-glucose

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

160 g (0.742 mole) of D-(+)-glucosamine hydrochloride were dissolved in 2200 ml of methanol (99.6% purity), and 187.9 g (1.86 mole) of triethylamine were added to the resulting solution. 115.9 g of ethyl trifluoroacetate were then added dropwise to the resulting mixture, whilst ice-cooling, after which the mixture was stirred overnight at room temperature. At the end of this time, the mixture was concentrated by evaporation under reduced pressure, and then benzene (250 ml twice) and ethyl acetate (250 ml) were repeatedly added to the residue, which was then concentrated by evaporation under reduced pressure and then finally dried sufficiently in vacuo. The whole of the resulting crude trifluoroacetyl compound was used in the subsequent step (b) without purification.

후처리

  1. temperaturecooling
  2. concentrationAt the end of this time, the mixture was concentrated by evaporation under reduced pressure
  3. additionbenzene (250 ml twice) and ethyl acetate (250 ml) were repeatedly added to the residue, which
  4. concentrationwas then concentrated by evaporation under reduced pressure
  5. customfinally dried sufficiently in vacuo
  6. customThe whole of the resulting crude trifluoroacetyl compound was used in the subsequent step (b) without purification

출처 및 근거

ORD 기록
ord-3a915aac78f24bb3ba0b12eecf7d906b
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05792840

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