Acetic Acid → H-D-Trp-D-Phe-OMe

HRID 596350노트

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HRID 596350 반응식
[NH:1](C(OCC1C=CC=CC=1)=O)[C@@H:2]([C:13]([NH:15][C@@H:16]([C:24]([OH:26])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[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.[H][H].[C:39](O)(=O)C>[Pd]>[NH2:1][C@@H:2]([C:13]([NH:15][C@@H:16]([C:24]([O:26][CH3:39])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[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

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 92274633Z-D-Trp-D-PheHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 131710658H-D-Trp-D-Phe-OMe

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

A mixture of Z-D-Trp-D-Phe-Ome (2.00 g, 4.0 mmoles, described in Example 6) and 5% Pd/C (0.25 g) in acetic acid is stirred rapidly under an atmosphere of hydrogen. After completion of hydrogen uptake a stream of nitrogen is passed through the mixture for 15 min, the catalyst is removed by filtration, and the acetic acid is removed under reduced pressure. The residue is taken into benzene, evaporated under reduced pressure (twice), and dried under reduced pressure over KOH pellets to give H-D-Trp-D-Phe-OMe.CH3CO2H. The above product is dissolved in dry DMF (20 ml) and cooled to 0° C. N-ethylmorpholine (0.512 ml, 4 mmoles) is added, followed by ##STR97## (2.00 g, 4 mmoles). The solution is stirred at 0° C for 30 min and for 3 days at room temperature. The solvent is evaporated under reduced pressure, the residue is taken into EtOAc and washed with cold saturated NaHCO3 solution, water, cold citric acid (2N), water, saturated NaHCO3 solution and saturated NaCl solution. The EtOAc solution is dried with MgSO4 and evaporated under reduced pressure to afford the crude title product. After chromatography on a column of silica gel (300 g) with CHCl3 containing MeOH (5%) and pyridine (0.1%) as eluent, the chromatographically pure product is triturated with ether, filtered, dried under reduced pressure, and crystallized from MeOH-CH2Cl2 -isopropyl ether to give the title compound; mp 172° - 174° C, [α]D25 = +18.9° (c = 1, DMF).

후처리

  1. customthe catalyst is removed by filtration
  2. customthe acetic acid is removed under reduced pressure
  3. customevaporated under reduced pressure (twice), and
  4. dry with materialdried under reduced pressure over KOH pellets

출처 및 근거

ORD 기록
ord-2d657137a1b841b0a0c9eb8fd3703991
출처 데이터셋
uspto-grants-1977_03
특허 번호
US04010260

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