Citric Acid → HCID 14336499、化合物

HRID 1708831ノート

反応式

HRID 1708831 の反応式
O.[C:2]([NH:9][C@@H:10]([C:15]([OH:17])=O)[CH2:11][CH:12]([CH3:14])[CH3:13])([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:29]([O:36][C:37](=[O:43])[C@H:38]([CH:40]([CH3:42])[CH3:41])[NH2:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl(O)(=O)(=O)=O.C(N=C=NCCCN(C)C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.O>[CH2:29]([O:36][C:37](=[O:43])[C@H:38]([CH:40]([CH3:41])[CH3:42])[NH:39][C:15](=[O:17])[C@@H:10]([CH2:11][CH:12]([CH3:13])[CH3:14])[NH:9][C:2]([O:4][C:5]([CH3:6])([CH3:7])[CH3:8])=[O:3])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

参加物

9

反応物 6

HCID 311Citric AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2724763D-Leucine, N-[(1,1-dimethylethoxy)carbonyl]-, monohydrateHCID 11567066O-benzyl-L-valine toluene-p-sulphonateHCID 18959840HCID 18959840、化合物

生成物 1

HCID 14336499HCID 14336499、化合物収率 110.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

0.749 g (3.00 mmol) of Boc-D-leucine monohydrate, 1.252 g (3.30 mmol) of L-valine benzyl ester p-toluenesulfonate and 0.811 g (6.00 mmol) of N-hydroxy-benzotriazole were dissolved in 15 ml of dichloromethane. The resulting mixture was cooled with ice, and admixed with 0.504 ml (3.60 mmol) of triethylamine and 1.108 g (4.20 mmol) of 87% 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide perchlorate. The reaction mixture was stirred for 2 hours, and then further stirred at room temperature for 4 hours. After the completion of the reaction, 30 ml of water and 5 ml of a 1% aqueous citric acid solution were added to the reaction mixture. The crystals thus deposited were filtered off. The organic layer successively was washed with 20 ml of water, 20 ml of a saturated aqueous sodium hydrogen carbonate solution and 10 ml of water, dried over anhydrous sodium sulfate, and distilled to remove the solvent therefrom, whereby 1.390 g of crude Boc-D-leucyl-L-valine benzyl ester product were obtained as white crystals.

後処理

  1. temperatureThe resulting mixture was cooled with ice
  2. stirringfurther stirred at room temperature for 4 hours
  3. additionwere added to the reaction mixture
  4. filtrationThe crystals thus deposited were filtered off
  5. washThe organic layer successively was washed with 20 ml of water, 20 ml of a saturated aqueous sodium hydrogen carbonate solution and 10 ml of water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationdistilled
  8. customto remove the solvent

出典と根拠

ORDレコード
ord-61a5b9436fa14d5c904d94f5bfe54e59
出典データセット
uspto-grants-1994_10
特許番号
US05359138

反応ノート

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