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Dicyclohexylcarbodiimide → Z-Sta-Sar-His-Lys(Boc)-OMe

HRID 1982330
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HRID 1982330 반응식
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C@H:7]([CH2:9][C:10]([OH:12])=O)[OH:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH:23]([CH2:25][C:26]([NH:28][C@H:29]([C:36]([NH:38][C@H:39]([C:52]([O:54][CH3:55])=[O:53])[CH2:40][CH2:41][CH2:42][CH2:43][NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[O:37])[CH2:30][C:31]1[N:35]=[CH:34][NH:33][CH:32]=1)=[O:27])[CH3:24].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.O>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C@H:7]([CH2:9][C:10]([N:23]([CH2:25][C:26]([NH:28][C@H:29]([C:36]([NH:38][C@H:39]([C:52]([O:54][CH3:55])=[O:53])[CH2:40][CH2:41][CH2:42][CH2:43][NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[O:37])[CH2:30][C:31]1[N:35]=[CH:34][NH:33][CH:32]=1)=[O:27])[CH3:24])=[O:12])[OH:8])[CH2:3][CH:4]([CH3:5])[CH3:6]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 14560231Z-Sta-OHHCID 178484730HCID 178484730, 화합물

생성물 1

HCID 178501444Z-Sta-Sar-His-Lys(Boc)-OMe

시약·촉매·용매 2

HCID 962Water용매
HCID 6228Dimethylformamide용매

실험 절차

254 mg of Z-Sta-OH (see stage 1.12), 297 mg of H-Sar-His-Lys(Boc)-OMe, 97 mg of HOBt×H2O and 196 mg of DCCI are dissolved, in this sequence, in 3 ml of DMF and the whole is left to stand for 20 hours at room temperature. The DCH which has crystallised out is filtered off, the filtrate is concentrated to dryness, heated for 1 hour at 60° in 7 ml of methanol/glacial acetic acid/H2O (94:3:3), and this solution is again concentrated to dryness. The oily residue is purified by chromatography over 75 g of silica gel (Merck No. 60, 230-400 mesh) by elution with CHCl3 /MeOH (9:1). The pure fractions are dissolved in ethyl acetate, washed with NaHCO3 solution and with H2O and, by concentration of the organic phase, Z-Sta-Sar-His-Lys(Boc)-OMe is obtained in amorphous form (honey); Rf (F)=0.15; Rf (I)=0.5.

후처리

  1. waitthe whole is left
  2. customThe DCH which has crystallised out
  3. filtrationis filtered off
  4. concentrationthe filtrate is concentrated to dryness
  5. temperatureheated for 1 hour at 60° in 7 ml of methanol/glacial acetic acid/H2O (94:3:3)
  6. concentrationthis solution is again concentrated to dryness
  7. customThe oily residue is purified by chromatography over 75 g of silica gel (Merck No. 60, 230-400 mesh) by elution with CHCl3 /MeOH (9:1)
  8. dissolutionThe pure fractions are dissolved in ethyl acetate
  9. washwashed with NaHCO3 solution and with H2O and, by concentration of the organic phase

출처 및 근거

ORD 기록
ord-bca7bad91e344a1c8ebbcd2e163fdf46
출처 데이터셋
uspto-grants-1986_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04595677

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