9-Fluorenylmethyl chloroformate → N-Fmoc-2-(trans-Dec-4-en-1-ylamino)acetaldehyde dimethyl acetal

HRID 498164ノート

反応式

HRID 498164 の反応式
[CH3:1][O:2][CH:3]([O:16][CH3:17])[CH2:4][NH:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C(N(C(C)C)CC)(C)C.[C:27](Cl)([O:29][CH2:30][CH:31]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37]2[C:32]1=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:28].OS([O-])(=O)=O.[K+]>ClCCl>[CH3:17][O:16][CH:3]([O:2][CH3:1])[CH2:4][N:5]([CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:27]([O:29][CH2:30][CH:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:38]2[C:43]1=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:28]

参加物

6

反応物 4

HCID 343679-Fluorenylmethyl chloroformateHCID 81531DiisopropylethylamineHCID 516920Potassium bisulfateHCID 219663022-(trans-Dec4-en-1-ylamino)acetaldehyde dimethyl acetal

生成物 1

HCID 21966301N-Fmoc-2-(trans-Dec-4-en-1-ylamino)acetaldehyde dimethyl acetal収率 80.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(trans-Dec-4-en-1-ylamino)acetaldehyde dimethyl acetal (10.5 g, 43.2 mmol) was mixed with dichloromethane (300 mL) and 7.5 mL (43.2 mmol) diisopropylethyl amine and 11.2 g (43.2 mmol) of FMOC-Cl was added portionwise. The reaction was stirred at room temperature for 3 hours and then poured into a solution of 10% KHSO4 (200 mL). The organic layer was washed with water (200 mL), dried over MgSO4, and concentrated under reduced pressure. The resulting oil was chromatographed on silica gel in 10% EtOAc/Hexanes to give 16.1 g (34.6 mmol) of N-Fmoc-2-(trans-dec-4-en-1-ylamino)acetaldehyde dimethyl acetal as a clear oil that was used directly in the next step.

後処理

  1. additionwas added portionwise
  2. washThe organic layer was washed with water (200 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting oil was chromatographed on silica gel in 10% EtOAc/Hexanes

出典と根拠

ORDレコード
ord-32d7cd5112ee4f8783f689fedeb39af4
出典データセット
uspto-grants-2005_09
特許番号
US06949681B2

反応ノート

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