Hydrochloric Acid → HCID 86585087, 화합물

HRID 1760889노트

반응식

HRID 1760889 반응식
[CH3:1][C:2]([O:4][CH2:5][C@H:6]1[O:11][CH:10]=[C:9](OC(C)=O)[C@@H:8]([O:16][C:17]([CH3:19])=[O:18])[C@@H:7]1[O:20][C:21]([CH3:23])=[O:22])=[O:3].N1C=CC=CC=1.Cl.C(Cl)(Cl)Cl.[OH:35][NH2:36]>>[C:17]([O:16][C@H:8]1[C@H:7]([O:20][C:21](=[O:22])[CH3:23])[C@@H:6]([CH2:5][O:4][C:2](=[O:3])[CH3:1])[O:11][CH2:10][C:9]1=[N:36][OH:35])(=[O:18])[CH3:19]

참가 물질

6

반응물 5

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 1049PyridineHCID 6212Chloroform2회HCID 27347382,3,4,6-Tetra-O-acetyl-2-hydroxy-D-glucal

생성물 1

HCID 86585087HCID 86585087, 화합물

실험 절차

[litt=F. W. Lichtenthaler and P. Jarglis. Tetrahedron Letters 21 (1980) 1425-1428] To a solution of 2,3,4,6-tetra-O-acetyl-2-hydroxy-D-glucal (7.90 g, 23.9 mmol) in dry pyridine (40 mL, 496 mmol), HONH2, HCl (5.85 g, 84.2 mmol) was added and the mixture was stirred for 24 h. The reaction mixture was concentrated and dissolved in CHCl3 (300 mL). The organic phase was washed with 1 M HCl (aq., 75 mL), sat. aq. NaHCO3 (75 mL) and H2O (75 mL), dried (MgSO4) and evaporated to a syrup of 2, (7.19 g, 99%). By addition of a small volume of EtOH the product crystallysed (4.43 g, 61%, mp 86-89° C.). Two recrystallisations from toluene afforded an analytical sample: mp 90-92° C.; [α]D−39.4° (c 1.3, CHCl3) [Lit. mp 89-90° C., [α]D−39.0 (c 0.4, CHCl3)].

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in CHCl3 (300 mL)
  3. washThe organic phase was washed with 1 M HCl (aq., 75 mL), sat. aq. NaHCO3 (75 mL) and H2O (75 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a syrup of 2, (7.19 g, 99%)
  6. additionBy addition of a small volume of EtOH the product
  7. customTwo recrystallisations from toluene
  8. customafforded an analytical sample

출처 및 근거

ORD 기록
ord-c2c654a76d65450f99f8b801894b52b4
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06846505B2

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