Nitrogen → 2(S)-Boc-amino-1-(5-methoxymethyl-1,3,4-oxadiazol-2-yl)-1-butanol

HRID 1444578노트

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HRID 1444578 반응식
[CH3:1][O:2][CH2:3][C:4]1[O:5][CH:6]=[N:7][N:8]=1.[Li]CCCC.[N:14]#N.CCOCC.[C:21]([C@:28](N)([CH2:31][CH3:32])[CH:29]=[O:30])([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>C1COCC1>[C:21]([C@@H:28]([CH2:31][CH3:32])[C:29]([NH2:14])([C:6]1[O:5][C:4]([CH2:3][O:2][CH3:1])=[N:8][N:7]=1)[OH:30])([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

참가 물질

7

반응물 5

HCID 947NitrogenHCID 3283Diethyl EtherHCID 219626882-(Methoxymethyl)-1,3,4-oxadiazoleHCID 86590935(S)-2-Boc-aminobutyraldehydeHCID 178418339Butyllithium

생성물 1

HCID 694511442(S)-Boc-amino-1-(5-methoxymethyl-1,3,4-oxadiazol-2-yl)-1-butanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-45 °C

실험 절차

To a stirred solution of 2-methoxymethyl-1,3,4-oxadiazole (4.6 g, 40 mmol) in THF (100 mL) was added n-BuLi (1.6 M solution in 25.2 mL of hexane) dropwise under N2 at −78° C. After 1 h, MgBr.Et2O (10.4 g, 40.3 mmol) was added and the reaction mixture was allowed to warm to −45° C. for 1 h before being treated with 2(S)-Boc-aminobutyraldehyde (5.28 g, 28.25 mmol) in THF (20 mL). The reaction mixture was stirred for 1 h, quenched with saturated NH4Cl, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgSO4 and concentrated. The residue was purified by silica gel column chromatography to yield 2(S)-Boc-amino-1-(5-methoxymethyl-[1.3.4]-oxadiazol-2-yl)-1-butanol (500 mg).

후처리

  1. customquenched with saturated NH4Cl
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-ca32d1f6ad58478da574c924ebdf1e6a
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07662849B2

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