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Triethylamine → (2RS,3S)-3-tert-butyloxycarbonylamino-2-hydroxy-5-methylhexanoic acid

HRID 1722905
ノート
印刷プレビュー

反応式

HRID 1722905 の反応式
[NH2:1][C@@H:2]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:3]([OH:7])[C:4]([OH:6])=[O:5].C(N(CC)CC)C.[C:19]([O:23][C:24](ON=C(C1C=CC=CC=1)C#N)=[O:25])([CH3:22])([CH3:21])[CH3:20]>O.O1CCOCC1>[C:19]([O:23][C:24]([NH:1][C@@H:2]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:3]([OH:7])[C:4]([OH:6])=[O:5])=[O:25])([CH3:22])([CH3:21])[CH3:20]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 12879199(2RS,3S)-3-amino-2-hydroxy-5-methylhexanoic acid

生成物 1

HCID 13848631(2RS,3S)-3-tert-butyloxycarbonylamino-2-hydroxy-5-methylhexanoic acid収率 97.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回
HCID 31275
1,4-Dioxane
溶媒

実験手順

To a solution of 3.22 g of (2RS,3S)-3-amino-2-hydroxy-5-methylhexanoic acid and 3.08 ml of triethylamine in 30 ml of water was added a solution of 5.41 g of 2-(tert-butyloxycarbonyloxyimino)-2-phenylacetonitrile in 30 ml of dioxane, and the mixture was stirred for 16 hours at room temperature. To the reaction mixture was added 100 ml of water, and the mixture was extracted with ethyl acetate to remove neutral materials. The aqueous layer was acidified by the addition of an aqueous citric acid solution, and the acid solution was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 5.10 g of (2RS,3S)-3-tert-butyloxycarbonylamino-2-hydroxy-5-methylhexanoic acid as a pale yellow oil.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. customto remove neutral materials
  3. additionThe aqueous layer was acidified by the addition of an aqueous citric acid solution
  4. extractionthe acid solution was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-c128414d6a804fed8f8b04332b070d63
出典データセット
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04857650

反応ノート

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