Malic Acid → O-[4-(15-carbomethoxypentadecylamino)benzoyl]malic acid

HRID 904258ノート

反応式

HRID 904258 の反応式
C([N:11]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])[C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1)(OCC1C=CC=CC=1)=O.C(N(CC)CC)C.[C:47]([OH:55])(=[O:54])[CH:48]([CH2:50][C:51]([OH:53])=[O:52])[OH:49].[H][H]>O1CCCC1.[Pd].CCOCC>[C:36]([CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][NH:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([O:54][C:47](=[O:55])[CH:48]([CH2:50][C:51]([OH:53])=[O:52])[OH:49])=[O:17])=[CH:14][CH:13]=1)([O:38][CH3:39])=[O:37]

参加物

8

反応物 4

HCID 525Malic AcidHCID 8471TriethylamineHCID 21163259N-carbobenzyloxy-4-(15-carbomethoxypentadecylamino)benzoyl chlorideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 86737301O-[4-(15-carbomethoxypentadecylamino)benzoyl]malic acid

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a warm solution of N-carbobenzyloxy-4-(15-carbomethoxypentadecylamino)benzoyl chloride and 1.3 g. triethylamine in 100 ml. ether is added 2 g. malic acid. An immediate precipitate forms, but the mixture is refluxed for one hour and filtered while hot. The solid is washed several times with hot ether, then the ether is evaporated to yield a white solid. The product is dissolved in tetrahydrofuran (100 ml.) and hydrogenated over 600 mg. 10% palladium-on-carbon at 50 psi until hydrogen uptake stops. The catalyst is filtered, the solution is evaporated, and the residue is crystallized from acetic acid to yield the title compound as a tan, crystalline mass.

後処理

  1. temperatureAn immediate precipitate forms, but the mixture is refluxed for one hour
  2. filtrationfiltered while hot
  3. washThe solid is washed several times with hot ether
  4. customthe ether is evaporated
  5. customto yield a white solid
  6. filtrationThe catalyst is filtered
  7. customthe solution is evaporated
  8. customthe residue is crystallized from acetic acid

出典と根拠

ORDレコード
ord-6444ee9112c346d88f949c7cbc66c35b
出典データセット
uspto-grants-1980_10
特許番号
US04230628

反応ノート

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