Tyr(3-tBu)-OMe → Z-Phg-Tyr(3-tBu)-OMe

HRID 1383730노트

반응식

HRID 1383730 반응식
[NH:1]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C@H:2]([C:9]([O:11]N1C(=O)CCC1=O)=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:29][C@H:30]([C:43]([O:45][CH3:46])=[O:44])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([C:39]([CH3:42])([CH3:41])[CH3:40])[CH:33]=1>CN(C=O)C.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[NH:1]([C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])[C@H:2]([C:9]([NH:29][C@H:30]([C:43]([O:45][CH3:46])=[O:44])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([C:39]([CH3:42])([CH3:40])[CH3:41])[CH:33]=1)=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

6

반응물 2

HCID 15549498Tyr(3-tBu)-OMeHCID 51341853(S)-2,5-Dioxopyrrolidin-1-yl 2-(((benzyloxy)carbonyl)amino)-2-phenylacetate

생성물 1

HCID 131722747Z-Phg-Tyr(3-tBu)-OMe

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of Z-Phg-OSu (640 mg) in DMF (10 ml), 463 mg (1.84 mmol) of Tyr(3-tBu)-OMe and 408 mg (3.34 mmol) of DMAP were added and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate and washed first with saturated aqueous NaHCO3, then with water and finally with saturated brine. The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate:n-hexane=1:1) to give Z-Phg-Tyr(3-tBu)-OMe in the amount of 905 mg (quantitative).

후처리

  1. washwashed first with saturated aqueous NaHCO3
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washthe resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate:n-hexane=1:1)

출처 및 근거

ORD 기록
ord-3cc502e63ea24b6fb7aa6f8530252ef3
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06255285B1

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