Citric Acid → HCID 14336499, 화합물

HRID 1708831노트

반응식

HRID 1708831 반응식
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

참가 물질

9

반응물 6

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

생성물 1

HCID 14336499HCID 14336499, 화합물수율 110.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-61a5b9436fa14d5c904d94f5bfe54e59
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05359138

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