Imidazole → 2-bromo-(R)-1-tert-butyldimethylsiloxy-1-(3-formamido-4-benzyloxyphenyl)ethane

HRID 1367784

반응식

HRID 1367784 반응식
[Br:1][CH2:2][C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([NH:19][CH:20]=[O:21])[CH:6]=1)[OH:4].N1C=CN=C1.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].C([Si](Cl)(C)C)CCC>CN(C)C=O.C(OC(C)C)(=O)C>[CH2:12]([O:11][C:8]1[CH:9]=[CH:10][C:5]([C@@H:3]([O:4][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:2][Br:1])=[CH:6][C:7]=1[NH:19][CH:20]=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

7

반응물 4

HCID 795Imidazole2회HCID 28928tert-Butyldimethylsilyl chlorideHCID 66079N-ButylchlorodimethylsilaneHCID 11142645(R)-N-[5-(2-Bromo-1-hydroxyethyl)-2-(phenylmethoxy)phenyl]formamide

생성물 1

HCID 574610672-bromo-(R)-1-tert-butyldimethylsiloxy-1-(3-formamido-4-benzyloxyphenyl)ethane수율 68%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 7915Isopropyl Acetate용매

실험 절차

(R)-2-Bromo-1-(3-formamido-4-benzyloxyphenyl)ethanol (9.9 g, 28 mmol) was dissolved in dimethylformamide (36 mL). Imidazole (2.3 g, 34 mmol) and tert-butyldimethylsilyl chloride (4.7 g, 31 mmol) were added. The solution was stirred under nitrogen atmosphere for 72 h. Additional imidazole (0.39 g, 5.7 mmol) and tent-butyldimethylsilyl chloride (0.64 g, 4.3 mmol) were added and the reaction was stirred for an additional 20 h. The reaction mixture was then diluted with a mixture of isopropyl acetate (53 mL) and hexanes (27 mL) and transferred to a separatory funnel. The organic layer was washed twice with a mixture of water (27 mL) and saturated aqueous sodium chloride (27 mL) followed by a final wash with saturated aqueous sodium chloride (27 mL). The organic layer was dried over sodium sulfate. Silica gel (23.6 g) and hexanes (27 mL) were added and the suspension was stirred for 10 min. The solids were removed by filtration and the filtrate concentrated under vacuum. The residue was crystallized from hexanes (45 mL) to afford 8.85 g (19 mmol, 68%) of the title compound as a solid. MS m/z: [M+H+] calcd for C22H30NO3SiBr 464.1; found 464.2.

후처리

  1. stirringthe reaction was stirred for an additional 20 h
  2. customtransferred to a separatory funnel
  3. washThe organic layer was washed twice with a mixture of water (27 mL) and saturated aqueous sodium chloride (27 mL)
  4. washa final wash with saturated aqueous sodium chloride (27 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. additionSilica gel (23.6 g) and hexanes (27 mL) were added
  7. stirringthe suspension was stirred for 10 min
  8. customThe solids were removed by filtration
  9. concentrationthe filtrate concentrated under vacuum
  10. customThe residue was crystallized from hexanes (45 mL)

출처 및 근거

ORD 기록
ord-3eb5ae0c1b0949628f20836534366d1e
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893256B2

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