Tetrahydrofuran → HCID 66921872, 화합물

HRID 1364014노트

반응식

HRID 1364014 반응식
[Br:1][C:2]1[C@@H:7](O)[C@@H:6]([OH:9])[C@@H:5]([NH:10][C:11](=[O:13])[CH3:12])[C@H:4]([O:14][CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH:3]=1.C(OC(C)(C)C([Br:27])=O)(=O)C.C1C[O:33][CH2:32][CH2:31]1>>[C:32]([O:9][C@H:6]1[C@@H:5]([NH:10][C:11](=[O:13])[CH3:12])[C@H:4]([O:14][CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH:3]=[C:2]([Br:1])[C@@H:7]1[Br:27])(=[O:33])[CH3:31]

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 27247151-Bromocarbonyl-1-methylethyl acetateHCID 25019473HCID 25019473, 화합물

생성물 1

HCID 66921872HCID 66921872, 화합물

실험 절차

To a stirred solution of diol 23 (7.42 g, 22.1 mmol) in THF (150 mL) at 0° C. under nitrogen atmosphere, α-acetoxyisobutyryl bromide (4.1 mL, 27.8 mmol) was added dropwise over a period of 10 min. The reaction mixture was stirred at same temperature for 30 min, and warmed to room temperature with stirring for 3.5 h. The solvent was evaporated, and the residual oil was partitioned between EtOAc (200 mL) and 5% aqueous NaHCO3 (50 mL). The organic layer was washed with water (100 mL), dried over MgSO4, filtered and concentrated to afford the crude bromoacetate 24 (9.05 g). The crude product was used in the next step without further purification.

후처리

  1. stirringwith stirring for 3.5 h
  2. customThe solvent was evaporated
  3. customthe residual oil was partitioned between EtOAc (200 mL) and 5% aqueous NaHCO3 (50 mL)
  4. washThe organic layer was washed with water (100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e2e8382a46104cf7afb321f156115f6d
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888337B2

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