4-Methylmorpholine → HCID 57571330、化合物

HRID 1971291ノート

反応式

HRID 1971291 の反応式
[C:1]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[N:21]1[CH2:26][CH2:25]O[CH2:23][CH2:22]1.ClC(OCC(C)C)=O.N1CCCC1>C1COCC1>[O:19]=[C:17]([N:21]1[CH2:26][CH2:25][CH2:23][CH2:22]1)[C@@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH2:10][C:11]1[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=1

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 31268PyrrolidineHCID 62365Isobutyl chloroformateHCID 7020844(2S)-2-(((tert-butoxy)carbonyl)amino)-3-(pyridin-4-yl)propanoic acid

生成物 1

HCID 57571330HCID 57571330、化合物収率 28%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-15 °C

実験手順

To a solution of N-Boc-(2S)-3-(pyridin-4-yl)alanine (500 mg, 1.9 mmol) in THF (12 mL) was added N-methylmorpholine (200 μL, 1.9 mmol) and the solution was stirred for 5 min, cooled at −15° C. and treated dropwise with isobutyl chloroformate (249 μL, 1.9 mmol). The mixture was stirred for 10 min and pyrrolidine (1.08 g, 15.2 mmol) was added and allowed to warm to 25° C. with stirring for 3 h. The solvent were removed under reduced pressure and the residue was partitioned between EtOAc and NaH2PO4 pH=7.2. The aqueous layer was discarded and the organic layer was washed with aqueous saturated NaHCO3, dried over Na2SO4, filtered and evaporated. The resulting solid was purified by column chromatography (SiO2) with a gradient of 0% to 10% [v/v] MeOH in EtOAc to give tert-butyl (S)-1-oxo-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-2-ylcarbamate EBE 06190 (167 mg, 28% yield) as a white solid.

後処理

  1. stirringThe mixture was stirred for 10 min
  2. temperatureto warm to 25° C.
  3. stirringwith stirring for 3 h
  4. customThe solvent were removed under reduced pressure
  5. customthe residue was partitioned between EtOAc and NaH2PO4 pH=7.2
  6. washthe organic layer was washed with aqueous saturated NaHCO3
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe resulting solid was purified by column chromatography (SiO2) with a gradient of 0% to 10% [v/v] MeOH in EtOAc

出典と根拠

ORDレコード
ord-fb6fbc5634ba4373af558ba0ae5cddfb
出典データセット
uspto-grants-2013_04
特許番号
US08431599B2

反応ノート

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