4-Methylmorpholine → tert-butyl N-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamate

HRID 427380ノート

反応式

HRID 427380 の反応式
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6](O)=[O:7])[CH:3]([CH3:5])[CH3:4].CN1CCOCC1.ClC(OCC(C)C)=O>COCCOC>[C:9]([NH:1][C@H:2]([CH2:6][OH:7])[CH:3]([CH3:4])[CH3:5])([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10]

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 83693Boc-L-Valine

生成物 1

HCID 7021464tert-butyl N-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamate収率 86.5%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

In 5 ml of 1,2-dimethoxyethane (DME), 1.086 g of Boc-Val-OH was dissolved and 550 μl of N-methylmorpholine and 650 μl of isobutyl chloroformate were successively added dropwise at −15° C. After stirring for 1 min, N-methylmorpholine hydrochloride was filtered off and washed twice with 2.5 ml each of DME. The filtrate and washings were combined and a solution of 284 mg of sodium borohydride in 2.5 ml of water was added in one portion. After 30 sec, 125 ml of water was added and the mixture was extracted with 25 ml of ethyl acetate and dried over anhydrous sodium sulfate. The dried solution was evaporated under reduced pressure to give 879 mg of the title compound.

後処理

  1. filtrationN-methylmorpholine hydrochloride was filtered off
  2. washwashed twice with 2.5 ml each of DME
  3. additiona solution of 284 mg of sodium borohydride in 2.5 ml of water was added in one portion
  4. waitAfter 30 sec
  5. addition125 ml of water was added
  6. extractionthe mixture was extracted with 25 ml of ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe dried solution was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-6ec3650917664dee9204e80629af4523
出典データセット
uspto-grants-2001_11
特許番号
US06313094B1

反応ノート

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