Ethyl Acetate → Methyl(2S)-2-[(22S)-5-acetyl-17-fluoro-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2, 4, 6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]-2-(tert-butoxy)acetate

HRID 1482147노트

반응식

HRID 1482147 반응식
[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[C:39]([C:42](C)=[CH2:43])[C:38]2=[N:45][C:35]3=[CH:36][N:37]2[C:12]=1[N:13]1[CH2:50][CH2:49][C:16]([CH3:51])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:48])[O:23][C:24]2[CH:25]=[CH:26][C:27]([F:47])=[CH:28][C:29]=2[C:30]2[CH:46]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:15][CH2:14]1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:53].[Na+].CC(=O)OCC>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[C:42]([C:39]1[C:38]2=[N:45][C:35]3=[CH:36][N:37]2[C:12]([N:13]2[CH2:14][CH2:15][C:16]([CH3:51])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:48])[O:23][C:24]4[CH:25]=[CH:26][C:27]([F:47])=[CH:28][C:29]=4[C:30]4[CH:46]=[C:34]3[CH:33]=[CH:32][CH:31]=4)[CH2:49][CH2:50]2)=[C:11]([C@H:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[C:7]([O:9][CH3:10])=[O:8])[C:40]=1[CH3:41])(=[O:53])[CH3:43]

참가 물질

7

반응물 3

HCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 118316348Methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-4,22,28-trimethyl-5-(prop-1-en-2-yl)-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate

생성물 1

HCID 118316383Methyl(2S)-2-[(22S)-5-acetyl-17-fluoro-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2, 4, 6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]-2-(tert-butoxy)acetate

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

Methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-4,22,28-trimethyl-5-(prop-1-en-2-yl)-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate (45 mg, 0.064 mmol, 1 equiv) was dissolved in dioxane (1934 μl) and water (645 μl). To this solution was added sodium periodate (444 mg, 2.076 mmol, 3.5 equiv) and 4% osmium tetraoxide (372 μl, 0.030 mmol, 0.05 equiv). The mixture was stirred at r.t. for 2 hours. Yellow solid was observed in the meantime. To the mixture was added water (20 mL) and EA (20 mL). The aqueous layer was separated. the organic layer was washed by brine, dried over MgSO4, filtered and concentrated to give a yellow oil, which is used as is for the next reaction. LCMS (ESI, M+1): 700.3.

후처리

  1. customThe aqueous layer was separated
  2. washthe organic layer was washed by brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow oil, which
  7. customas is for the next reaction

출처 및 근거

ORD 기록
ord-81dc85493c304b0b8d5cf8bb4a6e72bc
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409922B2

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