Cyanogen Bromide → (S)-4-((S)-2-Phenylbutyl)-4,5-dihydrooxazol-2-amine

HRID 1911567노트

반응식

HRID 1911567 반응식
[NH2:1][C@@H:2]([CH2:5][C@@H:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:7][CH3:8])[CH2:3][OH:4].C([O-])(=O)C.[Na+].[N:20]#[C:21]Br>CO>[C:9]1([C@@H:6]([CH2:7][CH3:8])[CH2:5][C@H:2]2[CH2:3][O:4][C:21]([NH2:20])=[N:1]2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

참가 물질

5

반응물 3

HCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 66705857(2S,4S)-2-amino-4-phenylhexan-1-ol

생성물 1

HCID 24963286(S)-4-((S)-2-Phenylbutyl)-4,5-dihydrooxazol-2-amine

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

To a stirred, cooled (0° C.) solution of (2S,4S)-2-amino-4-phenyl-hexan-1-ol (270 mg, 1.40 mmol) and sodium acetate (229 mg, 2.70 mmol) in methanol (20 ml) was added dropwise a solution of cyanogen bromide (180 mg, 1.68 mmol) in methanol (2 ml) over 10 min. The mixture was then allowed to warm to r.t. and stirring was continued for 16 h. The mixture was concentrated in vacuo and the residue was taken up in ethyl acetate and washed sequentially with saturated aqueous sodium bicarbonate solution and with saturated brine. The organic phase was dried over sodium sulphate and concentrated in vacuo. The residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: heptane/EtOAc/MeOH) to yield a light yellow solid. MS (ISP): 219.3 ([M+H]+).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. washwashed sequentially with saturated aqueous sodium bicarbonate solution and with saturated brine
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: heptane/EtOAc/MeOH)
  6. customto yield a light yellow solid

출처 및 근거

ORD 기록
ord-29d605716ea4403a9ee03c29b9e3d5b8
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604061B2

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