Tetrahydrofuran → HCID 66921872、化合物

HRID 1364014ノート

反応式

HRID 1364014 の反応式
[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]

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 27247151-Bromocarbonyl-1-methylethyl acetateHCID 25019473HCID 25019473、化合物

生成物 1

HCID 66921872HCID 66921872、化合物

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e2e8382a46104cf7afb321f156115f6d
出典データセット
uspto-grants-2011_02
特許番号
US07888337B2

反応ノート

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