(R)-(+)-N-(tert-Butoxycarbonyl)-O-(tert-butyldimethylsilyl)serinol → HCID 178454221, 화합물

HRID 82763

반응식

HRID 82763 반응식
[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]

참가 물질

5

반응물 3

HCID 10913779(R)-(+)-N-(tert-Butoxycarbonyl)-O-(tert-butyldimethylsilyl)serinolHCID 23665647Potassium tert-butoxideHCID 178441319HCID 178441319, 화합물

생성물 1

HCID 178454221HCID 178454221, 화합물수율 69.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-092630b413da4ad78796f56ff50981ec
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846730B2

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