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Hydrochloric Acid → N-benzyloxy-2-ethoxy-3-[4-(2-{4-methanesulfonyloxy-phenyl}ethoxy)phenyl]propanoic amide

HRID 987230
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HRID 987230 반응식
C1CCC(N=C=NC2CCCCC2)CC1.[OH:16][N:17]1C(=O)CCC1=O.[CH2:24]([O:26][CH:27]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([O:47][S:48]([CH3:51])(=[O:50])=[O:49])=[CH:43][CH:42]=2)=[CH:34][CH:33]=1)[C:28]([OH:30])=O)[CH3:25].C(N(C(C)C)CC)(C)C.[CH2:61](NO)[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1.Cl>C(#N)C.CCCCCCC>[CH2:61]([O:16][NH:17][C:28](=[O:30])[CH:27]([O:26][CH2:24][CH3:25])[CH2:31][C:32]1[CH:33]=[CH:34][C:35]([O:38][CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([O:47][S:48]([CH3:51])(=[O:49])=[O:50])=[CH:43][CH:42]=2)=[CH:36][CH:37]=1)[C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 81531DiisopropylethylamineHCID 2794173BenzylhydroxylamineHCID 113387772-Ethoxy-3-[4-(2-{4-[(methanesulfonyl)oxy]phenyl}ethoxy)phenyl]propanoic acid

생성물 1

HCID 22988722
N-benzyloxy-2-ethoxy-3-[4-(2-{4-methanesulfonyloxy-phenyl}ethoxy)phenyl]propanoic amide
수율 66%

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 8900Heptane용매

실험 절차

DCC (1 g; 4.85 mmole) and N-hydroxy-succinimide acid (0.56 g; 4.85 mmole) were added to a solution of 2-ethoxy-3-[4-(2-{4-methanesulfonyloxyphenyl}ethoxy)phenyl]propanoic acid (described in Example 2) (1.65 g; 4.04 mmole) in acetonitrile (25 ml) at 0° C. After 1 hour a precipitate was filtered off and diisopropylethylamine (1.82 g; 14.1 mmole) and benzyl hydroxylamine (1.24 g; 8.08 mmole) dissolved in acetonitrile were added. After stirring overnight hydrochloric acid (2M) was added and the mixture was extracted with diethyl ether. The organic phase was washed with sodium carbonate solution and dried (magnesium sulfate). The solvent was removed and the crude product was purified by chromatography on silica gel using ethyl acetate:heptane (gradient 10-100% ethyl acetate) as eluant to give 1.36 g (yield 66%) of N-benzyloxy-2-ethoxy-3-[4-(2-{4-methanesulfonyloxy-phenyl}ethoxy)phenyl]propanoic amide.

후처리

  1. filtrationAfter 1 hour a precipitate was filtered off
  2. additionwere added
  3. additionwas added
  4. extractionthe mixture was extracted with diethyl ether
  5. washThe organic phase was washed with sodium carbonate solution
  6. dry with materialdried (magnesium sulfate)
  7. customThe solvent was removed
  8. customthe crude product was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-b75c8260ed934ba1bc63e58b2a917004
출처 데이터셋
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06630600B1

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