Cesium carbonate → N-{5-chloro-2-(oxiran-2-ylmethoxy)-4-[(triisopropylsilyl)oxy]phenyl}-cyclopentanecarboxamide

HRID 270132노트

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HRID 270132 반응식
[Cl:1][C:2]1[C:3]([O:17][Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])=[CH:4][C:5]([OH:16])=[C:6]([NH:8][C:9]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[N+](C1C=C(S(O[CH2:47][C@@H:48]2[CH2:50][O:49]2)(=O)=O)C=CC=1)([O-])=O>O1CCOCC1>[Cl:1][C:2]1[C:3]([O:17][Si:18]([CH:22]([CH3:24])[CH3:23])([CH:25]([CH3:27])[CH3:26])[CH:19]([CH3:20])[CH3:21])=[CH:4][C:5]([O:16][CH2:47][CH:48]2[CH2:50][O:49]2)=[C:6]([NH:8][C:9]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])[CH:7]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 68962023N-{5-chloro-2-hydroxy-4-[(triisopropylsilyl)oxy]phenyl}cyclopentanecarboxamide

생성물 1

HCID 86601494N-{5-chloro-2-(oxiran-2-ylmethoxy)-4-[(triisopropylsilyl)oxy]phenyl}-cyclopentanecarboxamide수율 17.8%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

N-{5-chloro-2-hydroxy-4-[(triisopropylsilyl)oxy]phenyl}cyclopentanecarboxamide (140 mg, 0.3 mmol) was dissolved in 1,4-dioxane (20 mL). Caesium carbonate (170 mg, 0.5 mmol) was added, followed by (2S)-oxiran-2-y-methyl 3-nitrobenzenesulfonate (90 mg, 0.3 mmol). After stirring over night at room temperature the mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and concentrated. Purification by HPLC on C18 (Xterra, 5 um, 19×50 mm; acetonitrile/water 60/40 to 100/0 over 15 min) yielded 25 mg (17%) of the titled intermediate compound.

후처리

  1. customwas partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water
  3. concentrationconcentrated
  4. customPurification by HPLC on C18 (Xterra, 5 um, 19×50 mm; acetonitrile/water 60/40 to 100/0 over 15 min)

출처 및 근거

ORD 기록
ord-63fe470f8d1c45e3b81622d5120c734a
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449475B2

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