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 1482147ノート

反応式

HRID 1482147 の反応式
[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]

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-81dc85493c304b0b8d5cf8bb4a6e72bc
出典データセット
uspto-grants-2016_08
特許番号
US09409922B2

反応ノート

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