Acetic Acid → (R)-tert-Butyl 3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-1-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

HRID 598880노트

반응식

HRID 598880 반응식
[CH3:1][C:2]1([CH3:32])[O:7][C:6](=[O:8])[CH:5]([C:9](=O)[C@@H:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[C:4](=[O:31])[O:3]1.C(O)(=O)C.[BH4-].[Na+]>C(Cl)Cl>[CH3:1][C:2]1([CH3:32])[O:3][C:4](=[O:31])[CH:5]([CH2:9][C@@H:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:16][CH:17]=2)[C:6](=[O:8])[O:7]1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 57950484(S)-tert-Butyl 1-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-1-oxo-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

생성물 1

HCID 57950499(R)-tert-Butyl 3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-1-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(S)-tert-Butyl 1-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-1-oxo-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (22.0 g, 48 mmol) in 200 mL DCM was cooled to −5° C. Acetic acid (32 g, 527 mmol) was added in one portion and sodium tetrahydroborate (4.5 g, 120 mmol) as a solid was added portion wise over about 40 minutes. The reaction mixture was stirred for another 40 minutes and the reaction mixture was stored in the freezer overnight and was then washed with brine (3×150 mL) and water (2×100 mL). The organic layer was dried over MgSO4. The desired product was obtained as a white amorphous solid (21.0 g, 98%). No further purification was performed and the reaction was carried on to the next step.

후처리

  1. additionwas added portion wise over about 40 minutes
  2. customwas stored in the freezer overnight
  3. washwas then washed with brine (3×150 mL) and water (2×100 mL)
  4. dry with materialThe organic layer was dried over MgSO4

출처 및 근거

ORD 기록
ord-988a214e692a413d8190a9403e8f62a2
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897619B2

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