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Ethylmorpholine → Z-D-Trp-D-Phe-OMe

HRID 596349
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HRID 596349 반응식
[NH:1]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@@H:2]([C:13](O)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH3:26][O:27][C:28]([C@H:30]([NH2:38])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29].Cl.ON1C2C=CC=CC=2N=N1.C(N1CCOCC1)C.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.CO.C(Cl)(Cl)Cl>[CH3:26][O:27][C:28](=[O:29])[C@@H:30]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[NH:38][C:13](=[O:14])[C@@H:2]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)[NH:1][C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 700663N-(Benzyloxycarbonyl)-D-tryptophanHCID 11481330methyl (2R)-2-amino-3-phenylpropanoate;hydrochloride

생성물 1

HCID 68125752Z-D-Trp-D-Phe-OMe

시약·촉매·용매

3
HCID 887Methanol용매HCID 6212Chloroform용매HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

A solution of Z-D-Trp-OH (3.62 g, 10.7 mmoles), H-D-Phe-Ome.HCl (2.3 g, 10.7 mmoles) and 1-hydroxybenzotriazole (2.89 g, 21.4 mmoles) in dry DMF (25 ml) is cooled to 0° C and N-ethylmorpholine (1.37 ml, 10.7 mmoles) is added. A cold (0° C) solution of DCC (2.27 g, 11 mmoles) in DMF (6 ml) is added dropwise and the reaction mixture is stirred for 1 hr at 0° C and 1 hr at room temperature. The reaction mixture is then cooled to 0° C, filtered, the filtrate evaporated under reduced pressure and taken upon in EtOAc. The EtOAc solution is washed with saturated NaHCO3 solution, water, cold citric acid (2N), water, saturated NaHCO3 solution and saturated NaCl solution, dried with MgSO4, and evaporated under reduced pressure to afford the crude title product which is subjected to chromatography on a column of silica gel (500 g) with CHCl3 containing MeOH (1%) as eluent. The eluates are evaporated under reduced pressure and the residue is crystallized from EtOAc-petroleum ether to give the title compound; mp 130° - 131° C, [α]D25 = +34.1° (c = 1, DMF).

후처리

  1. temperatureThe reaction mixture is then cooled to 0° C
  2. filtrationfiltered
  3. customthe filtrate evaporated under reduced pressure
  4. washThe EtOAc solution is washed with saturated NaHCO3 solution, water, cold citric acid (2N), water, saturated NaHCO3 solution and saturated NaCl solution
  5. dry with materialdried with MgSO4
  6. customevaporated under reduced pressure
  7. customto afford the crude title product which
  8. customThe eluates are evaporated under reduced pressure
  9. customthe residue is crystallized from EtOAc-petroleum ether

출처 및 근거

ORD 기록
ord-6f7a7986ca6b41c9b6d3648bf620668a
출처 데이터셋
uspto-grants-1977_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04010260

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