Triethylamine → (R)-alpha-[(3-Benzyloxycarbonylamino-3-methyl-1-oxobutyl)amino]benzenebutanoic acid allyl ester

HRID 1916

반응식

HRID 1916 반응식
[CH2:1]([O:4][C:5](=[O:16])[C@@H:6]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:7])[CH:2]=[CH2:3].C(N(CC)CC)C.[C:24]([O:28][C:29]([NH:31][C:32]([CH3:38])([CH3:37])[CH2:33][C:34]([OH:36])=O)=[O:30])([CH3:27])(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:50]2[CH:51]=C[CH:53]=[CH:54][C:49]=2N=N1>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]([O:4][C:5](=[O:16])[C@H:6]([NH:7][C:34](=[O:36])[CH2:33][C:32]([NH:31][C:29]([O:28][CH2:24][C:27]1[CH:53]=[CH:54][CH:49]=[CH:50][CH:51]=1)=[O:30])([CH3:37])[CH3:38])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH:2]=[CH2:3]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 103760463-((tert-Butoxycarbonyl)amino)-3-methylbutanoic acidHCID 22883347D-Homophenylalanine allyl ester

생성물 1

HCID 67665161(R)-alpha-[(3-Benzyloxycarbonylamino-3-methyl-1-oxobutyl)amino]benzenebutanoic acid allyl ester수율 59.7%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

D-Homophenylalanine allyl ester (350 mg; 1.60 mmol), triethylamine (445 μl; 3.19 mmol) and 3-t-butoxycarbonylamino-3-methylbutanoic acid (412.8 mg; 1.64 mmol) were dissolved in dry methylene chloride (3 ml) and stirred at room temperature to give a homogeneous solution. BOP was added to the solution over 5 minutes and the reaction mixture stirred together at room temperature for 12 h. The reaction mixture was quenched by adding brine (10 ml) directly to the reaction. The crude products were isolated by extraction with methylene chloride (2×25 ml); the combined methylene chloride extracts dried with powdered anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The pale yellow oil thus obtained was subjected to column chromatography on silica gel using an eluant of ethyl acetate and hexanes (1:1 v/v). In this way, 432 mg (59.7%) of the desired product was isolated as a colorless oil. FAB-MS: -calculated for C26H32N2O5 452.2; found 453.4 (M+1).

후처리

  1. customto give a homogeneous solution
  2. stirringthe reaction mixture stirred together at room temperature for 12 h
  3. customThe reaction mixture was quenched
  4. additionby adding brine (10 ml)
  5. customdirectly to the reaction
  6. dry with materialthe combined methylene chloride extracts dried with powdered anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe pale yellow oil thus obtained

출처 및 근거

ORD 기록
ord-f14a773ff3c34c0780dd20f31d997bc1
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726319

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