(R)-(+)-N-(tert-Butoxycarbonyl)-O-(tert-butyldimethylsilyl)serinol → HCID 178454221、化合物

HRID 82763

反応式

HRID 82763 の反応式
[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:23])[C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=2F)/[N:7]([CH2:24][C@@H:25]2[CH2:29][CH2:28][CH2:27][O:26]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Si:30]([O:37][CH2:38][C@H:39]([NH:42][C:43](=[O:49])[O:44][C:45]([CH3:48])([CH3:47])[CH3:46])[CH2:40][OH:41])([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31].CC(C)([O-])C.[K+]>C1COCC1>[Si:30]([O:37][CH2:38][C@H:39]([NH:42][C:43](=[O:49])[O:44][C:45]([CH3:48])([CH3:47])[CH3:46])[CH2:40][O:41][C:13]1[CH:14]=[CH:15][C:16]([C:18]([F:21])([F:19])[F:20])=[CH:17][C:12]=1[C:11](/[N:10]=[C:8]1\[S:9][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:6][N:7]\1[CH2:24][C@@H:25]1[CH2:29][CH2:28][CH2:27][O:26]1)=[O:23])([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]

参加物

5

反応物 3

HCID 10913779(R)-(+)-N-(tert-Butoxycarbonyl)-O-(tert-butyldimethylsilyl)serinolHCID 23665647Potassium tert-butoxideHCID 178441319HCID 178441319、化合物

生成物 1

HCID 178454221HCID 178454221、化合物収率 69.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A mixture of Example 32B (87 mg, 0.2 mmol), (R)-tert-butyl 2-{[tert-butyl(dimethyl)silyl]oxy}-1-(hydroxymethyl)ethylcarbamate (62 mg, 0.2 mmol) and 1N potassium tert-butoxide in THF (0.2 mL, 0.2 mmol) in THF (10 mL) was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure and the residue was partitioned between EtOAc and water. The organic layer was washed with brine, dried with MgSO4 and concentrated under reduced pressure to afford 100 mg of the title compound. MS (DCI/NH3) m/z 716 (M+H)+.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-092630b413da4ad78796f56ff50981ec
出典データセット
uspto-grants-2014_09
特許番号
US08846730B2

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