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1,2-Dichloroethane → 2-(Tert-butoxycarbonylamino)-4-methylpentyl 4-bromobutanoate

HRID 1776972
ノート
印刷プレビュー

反応式

HRID 1776972 の反応式
[OH:1][CH2:2][CH:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH:5]([CH3:7])[CH3:6].[Br:16][CH2:17][CH2:18][CH2:19][C:20](O)=[O:21].C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:16][CH2:17][CH2:18][CH2:19][C:20]([O:1][CH2:2][CH:3]([NH:8][C:9]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:15])[CH2:4][CH:5]([CH3:7])[CH3:6])=[O:21]
参加物反応条件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 111,2-DichloroethaneHCID 758094-Bromobutyric acidHCID 546110tert-butyl N-(1-hydroxy-4-methylpentan-2-yl)carbamate

生成物 1

HCID 866410002-(Tert-butoxycarbonylamino)-4-methylpentyl 4-bromobutanoate収率 97.9%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 6344
Dichloromethane
溶媒

反応条件

温度
0 °C

実験手順

tert-Butyl 1-hydroxy-4-methylpentan-2-ylcarbamate (2.00 g, 9.20 mmol) and 4-bromo-butyric acid (2.57 g, 15.38 mmol) were dissolved in CH2Cl2 (40 ml) and the mixture was cooled to 0° C. EDC (4.20 g, 21.90 mmol) and DMAP (0.27 g, 2.21 mmol) were added and the reaction was slowly warmed to room temperature and stirred overnight. Then the reaction was treated with a solution of 5% aqueous NaH2PO4 (100 ml). The organic layer was washed with a solution of 10% aqueous Na2CO3 (100 ml) and brine, dried over Na2SO4, filtered and concentrated. The obtained crude clear oil corresponding to the title compound (3.30 g) was used without any further purification.

後処理

  1. temperaturethe reaction was slowly warmed to room temperature
  2. washThe organic layer was washed with a solution of 10% aqueous Na2CO3 (100 ml) and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-255b1613995b4bd8b58083ebab237f3c
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09266820B2

反応ノート

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