Triethylamine → (R)-alpha-[(3-t-Butoxycarbonylamino-3-methyl-1-oxobutyl)amino]benzenebutanoic acid benzyl ester

HRID 1912

반응식

HRID 1912 반응식
[CH2:1]([O:8][C:9](=[O:20])[C@@H:10]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:28]([O:32][C:33]([NH:35][C:36]([CH3:42])([CH3:41])[CH2:37][C:38](O)=[O:39])=[O:34])([CH3:31])([CH3:30])[CH3:29].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>[CH2:1]([O:8][C:9](=[O:20])[C@H:10]([NH:11][C:38](=[O:39])[CH2:37][C:36]([NH:35][C:33]([O:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:34])([CH3:42])[CH3:41])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 103760463-((tert-Butoxycarbonyl)amino)-3-methylbutanoic acidHCID 15630399D-Homophenylalanine Benzyl ester

생성물 1

HCID 67665936(R)-alpha-[(3-t-Butoxycarbonylamino-3-methyl-1-oxobutyl)amino]benzenebutanoic acid benzyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

D-Homophenylalanine benzyl ester (725 mg; 3.23 mmol) whose preparation was described in Example 7 Step B, triethylamine (750 ml; 5,38 mmol) and 3-t-butoxycarbonylamino-3-methylbutanoic acid (585 mg; 2.69 mmol) were dissolved in dry methylene chloride (10 ml) and BOP (1.19 g, 2.69 mmol) was added with stirring in small batches to give a slightly cloudy solution. The reaction mixture was stirred at room temperature for 24 h then quenched by adding saturated brine (10 ml). The two phase system was extracted with methylene chloride (2×25 ml) and the combined methylene chloride extracts dried over magnesium sulfate powder, filtered and evaporated on a rotary evaporator under reduced pressure to give a cloudy, colorless oil. This material was taken up in the minimum volume of methylene chloride and chromatographed on silica gel using an eluant composed of ethyl acetate and hexanes in the ratio 1:1 v/v. The product was isolated after evaporation of the volatiles as a clear oil. The yield was 710 mg (88.5%). FAB-MS: -calculated for C27H36N2 O5 468.3; found 469.6 (M+1).

후처리

  1. customto give a slightly cloudy solution
  2. stirringThe reaction mixture was stirred at room temperature for 24 h
  3. customthen quenched
  4. additionby adding saturated brine (10 ml)
  5. extractionThe two phase system was extracted with methylene chloride (2×25 ml)
  6. dry with materialthe combined methylene chloride extracts dried over magnesium sulfate powder
  7. filtrationfiltered
  8. customevaporated on a rotary evaporator under reduced pressure
  9. customto give a cloudy, colorless oil
  10. customchromatographed on silica gel using an eluant
  11. customThe product was isolated
  12. customafter evaporation of the volatiles as a clear oil

출처 및 근거

ORD 기록
ord-a50f7cac2645481a8747ad859fb15edc
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726319

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