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

HRID 987230
ノート
印刷プレビュー

反応式

HRID 987230 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 6

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 8900Heptane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b75c8260ed934ba1bc63e58b2a917004
出典データセット
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06630600B1

反応ノート

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