4-Methylmorpholine → (S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

HRID 1473713ノート

反応式

HRID 1473713 の反応式
[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:2]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3][C:4](=O)[OH:5].CN1CCOCC1.ClC(OCC(C)C)=O.[BH4-].[Na+]>COCCOC.O>[C:17]([O:16][C:14]([NH:1][C@H:2]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3][CH2:4][OH:5])=[O:15])([CH3:19])([CH3:20])[CH3:18]

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 7010517(3S)-4-(tert-butoxy)-3-{[(tert-butoxy)carbonyl]amino}-4-oxobutanoic acid

生成物 1

HCID 11054918(S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
-15 °C

実験手順

To a solution of Boc-L-Asp-OtBu (3.00 g, 10.4 mmol) in 1,2-dimethoxyethane (10 mL) was added at −15° C. 4-methylmorpholine (1.14 mL, 10.4 mmol) and isobutyl chloroformate (1.35 mL, 10.4 mmol). After stirring for 10 min at −15° C. the precipitate was filtered off and washed with cold 1,2-dimethoxyethane (20 mL). To the filtrate was added at −15° C. a solution of sodium borohydride (0.59 g, 15.6 mmol) in water (5 mL). After 5 min water (250 mL) was added. The reaction mixture was extracted with ethyl acetate (3×100 mL), the combined organic layers dried over sodium sulphate, and concentrated under reduced pressure to give the title compound.

後処理

  1. filtrationwas filtered off
  2. washwashed with cold 1,2-dimethoxyethane (20 mL)
  3. extractionThe reaction mixture was extracted with ethyl acetate (3×100 mL)
  4. dry with materialthe combined organic layers dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-98c7d20b18214bd995fd50667892be43
出典データセット
uspto-grants-2015_04
特許番号
US09017645B2

反応ノート

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