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

HRID 1776972
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HRID 1776972 반응식
[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]
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참가 물질

6

반응물 3

HCID 111,2-DichloroethaneHCID 758094-Bromobutyric acidHCID 546110tert-butyl N-(1-hydroxy-4-methylpentan-2-yl)carbamate

생성물 1

HCID 866410002-(Tert-butoxycarbonylamino)-4-methylpentyl 4-bromobutanoate수율 97.9%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6344
Dichloromethane
용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-255b1613995b4bd8b58083ebab237f3c
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09266820B2

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