Tetrahydrofuran → HCID 66921872, compound

HRID 1364014Notes

Reaction equation

HRID 1364014 reaction equation
[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]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 27247152-Acetoxyisobutyryl bromideHCID 25019473HCID 25019473, compound

Product 1

HCID 66921872HCID 66921872, compound

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e2e8382a46104cf7afb321f156115f6d
Source dataset
uspto-grants-2011_02
Patent number
US07888337B2

Reaction notes

Loading…