Boc-Lys(Z)-OH → HCID 178454177, 화합물

HRID 223315노트

반응식

HRID 223315 반응식
[NH:1]1[CH2:19][CH2:18][CH2:17][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:13])[NH2:12])=[O:4].[C:20]([O:24][C:25]([NH:27][C@H:28]([C:44](O)=[O:45])[CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])=[O:26])([CH3:23])([CH3:22])[CH3:21]>O.O1CCOCC1>[C:20]([O:24][C:25]([NH:27][C@H:28]([C:44]([N:1]1[CH2:19][CH2:18][CH2:17][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:12])[NH2:13])=[O:4])=[O:45])[CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34]([O:36][CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)=[O:35])=[O:26])([CH3:23])([CH3:22])[CH3:21]

참가 물질

5

반응물 2

HCID 2724765Boc-Lys(Z)-OHHCID 178512874HCID 178512874, 화합물

생성물 1

HCID 178454177HCID 178454177, 화합물수율 74%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

23 g (0.086 mol) of prolyl-arginine (2) are dissolved in 100 ml of water and to this solution under stirring there is added a solution of 53 g (0.1 mol) of pentafluorophenyl ester of tert.butyloxycarbonyl-Nε -benzyloxycarbonyl-lysine in 300 ml of dioxane. 2 hours thereafter the solvent is evaporated and the residue is dissolved in 150 ml of dimethylformamide and stirred at room temperature (20° C.) for 48 hours. Then dimethylformamide is evaporated to 1/3 of its volume and the solution is poured into one liter of ether. After 2 hours the resulting residue is filtered-off, washed on the filter with ether and dried in vacuum. After reprecipitation from a mixture ethylacetate-ethanol-ether (3:1:30) there are obtained 47 g (74%) of the product (3) having the following properties: M.p. 90° C., [α]D20 -39.0° (c 1.0; 10% CH3COOH); Rf =0.51 (A, "Eastman"), 0.82 (B, "Eastman"); EHis =0.34 (pH=2.4).

후처리

  1. custom2 hours thereafter the solvent is evaporated
  2. dissolutionthe residue is dissolved in 150 ml of dimethylformamide
  3. stirringstirred at room temperature (20° C.) for 48 hours
  4. customThen dimethylformamide is evaporated to 1/3 of its volume
  5. additionthe solution is poured into one liter of ether
  6. washwashed on the
  7. filtrationfilter with ether
  8. customdried in vacuum
  9. customAfter reprecipitation from a mixture ethylacetate-ethanol-ether (3:1:30) there

출처 및 근거

ORD 기록
ord-4b96bb7dd51b48569ea38338652177fa
출처 데이터셋
uspto-grants-1982_10
특허 번호
US04353823

반응 노트

불러오는 중…