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

HRID 1444578ノート

反応式

HRID 1444578 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-45 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ca32d1f6ad58478da574c924ebdf1e6a
出典データセット
uspto-grants-2010_02
特許番号
US07662849B2

反応ノート

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