Triethylamine → (R)-alpha-[(2-Benzyloxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, allyl ester

HRID 1919

반응식

HRID 1919 반응식
[CH2:1]([O:4][C:5](=[O:18])[C@@H:6]([CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)[NH2:7])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH2:26]([O:33][C:34]([NH:36][C:37]([CH3:42])([C:39](O)=[O:40])[CH3:38])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl.C(OCC)(=O)C>[CH2:26]([O:33][C:34]([NH:36][C:37]([CH3:42])([CH3:38])[C:39]([NH:7][C@H:6]([CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:18])=[O:40])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 294936N-((Benzyloxy)carbonyl)-2-methylalanineHCID 7006689D-Tryptophan allyl ester

생성물 1

HCID 86752262(R)-alpha-[(2-Benzyloxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, allyl ester수율 84.5%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

D-Tryptophan allyl ester (250 mg; 0.822 mmol), triethylamine (230 μl; 1.650 mmol) and N-benzyloxycarbonyl-α-methylalanine (167.9 mg; 0.826 mmol) were dissolved in dry methylene chloride (5 ml) and BOP (363.7 mg; 0.822 mmol) added. The reaction mixture was stirred at room temperature for 16 h and then the reaction quenched with saturated brine (5 ml). The methylene chloride layer was separated, dried with magnesium sulfate and filtered then the volatiles removed under reduced pressure to leave a dark brown oil. Chromatography of this oil on silica gel using ethyl acetate and hexanes 2:1 v/v afforded 322 mg (84.5%) of the desired product. FAB-MS:- calculated for C26H29N3O5 463.2; found 464.5 (M+1).

후처리

  1. customthe reaction quenched with saturated brine (5 ml)
  2. customThe methylene chloride layer was separated
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customthe volatiles removed under reduced pressure
  6. customto leave a dark brown oil

출처 및 근거

ORD 기록
ord-275c3bd4a2eb43f196b2a4707e52cd1b
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726319

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