Ammonium fluoride → (4R)-13-hydroxy-11-methoxy-10-methyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)-3,4,5,6,7,9-hexahydro-1H-8,2,5-benzoxathiaazacycloundecine-6,9-dione

HRID 1082143노트

반응식

HRID 1082143 반응식
C[Si](C)(C(C)(C)C(C)C)[O:3][C:4]1[C:9]2[CH2:10][O:11][CH2:12][C@H:13]([C:21]3[O:25][N:24]=[C:23]([CH3:26])[N:22]=3)[NH:14][C:15](=[O:20])[CH2:16][S:17][C:18](=[O:19])[C:8]=2[C:7]([CH3:27])=[C:6]([O:28][CH3:29])[CH:5]=1.[F-].[NH4+]>CO.C(OCC)(=O)C>[OH:3][C:4]1[C:9]2[CH2:10][O:11][CH2:12][C@H:13]([C:21]3[O:25][N:24]=[C:23]([CH3:26])[N:22]=3)[NH:14][C:15](=[O:20])[CH2:16][S:17][C:18](=[O:19])[C:8]=2[C:7]([CH3:27])=[C:6]([O:28][CH3:29])[CH:5]=1

참가 물질

5

반응물 2

HCID 25516Ammonium fluorideHCID 67712984(4R)-13-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-11-methoxy-10-methyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)-3,4,5,6,7,9-hexahydro-1H-8,2,5-benzoxathiaazacycloundecine-6,9-dione

생성물 1

HCID 67712874(4R)-13-hydroxy-11-methoxy-10-methyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)-3,4,5,6,7,9-hexahydro-1H-8,2,5-benzoxathiaazacycloundecine-6,9-dione수율 90.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 268 mg of (4R)-13-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-11-methoxy-10-methyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)-3,4,5,6,7,9-hexahydro-1H-8,2,5-benzoxathiaazacycloundecine-6,9-dione in 10 ml of methanol were added 100 mg of ammonium fluoride, and the mixture was stirred for 30 min at room temperature. The mixture was diluted with 50 ml of ethyl acetate and washed with 30 ml of water and with 30 ml of brine. The organic layer was dried over sodium sulfate and the solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate, then hexane was added, and the white solid was isolated by filtration to give 178 mg of (4R)-13-hydroxy-11-methoxy-10-methyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)-3,4,5,6,7,9-hexahydro-1H-8,2,5-benzoxathiaazacycloundecine-6,9-dione as a white powder, m.p. 194°-196° C.

후처리

  1. washwashed with 30 ml of water and with 30 ml of brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. additionhexane was added
  6. customthe white solid was isolated by filtration

출처 및 근거

ORD 기록
ord-617c6580993c4ef9bac028dd6c63f022
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05589473

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