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Water → methyl (R)-3-tert-butoxycarbonylamino-2-(4-methanesulphonyl-piperazin-1-yl)propanoate

HRID 517500
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HRID 517500 반응식
Cl.[NH2:2][C@H:3]([CH2:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:4]([O:6][CH3:7])=[O:5].Cl[CH2:18][CH2:19][N:20]([CH2:25][CH2:26]Cl)[S:21]([CH3:24])(=[O:23])=[O:22].O>C(N(CC)C(C)C)(C)C>[C:13]([O:12][C:10]([NH:9][CH2:8][C@@H:3]([N:2]1[CH2:26][CH2:25][N:20]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:19][CH2:18]1)[C:4]([O:6][CH3:7])=[O:5])=[O:11])([CH3:16])([CH3:15])[CH3:14]
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참가 물질

5

반응물 3

HCID 962WaterHCID 245092n,n-Bis(2-chloroethyl)methanesulfonamideHCID 51358429(R)-Methyl 2-amino-3-((tert-butoxycarbonyl)amino)propanoate hydrochloride

생성물 1

HCID 67056910methyl (R)-3-tert-butoxycarbonylamino-2-(4-methanesulphonyl-piperazin-1-yl)propanoate수율 44.1%

시약·촉매·용매 1

HCID 81531Diisopropylethylamine
용매

실험 절차

A solution of 6 g (23.6 mmol) of methyl (R)-2-amino-3-tert-butoxycarbonylaminopropanoate hydrochloride and 5.2 g (23.6 mmol) of N,N-bis(2-chloroethyl)methanesulphonamide in 80 ml of N,N-diisopropylethylamine is heated at 125° C. with vigorous stirring for 18 h. After addition of water, the product is extracted with ethyl acetate. The organic phases are combined, washed with water, dried over magnesium sulphate, filtered and concentrated under vacuum. The crude product obtained is purified by chromatography over silica gel eluted with a 5/5 heptane/ethyl acetate mixture. 3.8 g (44%) of methyl (R)-3-tert-butoxycarbonylamino-2-(4-methanesulphonylpiperazin-1-yl)propanoate are obtained in the form of a white solid.

후처리

  1. extractionthe product is extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude product obtained
  7. customis purified by chromatography over silica gel
  8. washeluted with a 5/5 heptane/ethyl acetate mixture

출처 및 근거

ORD 기록
ord-9bb9523c700248b9a01547df2c48ab39
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115102B2

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