Triethylamine → (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(isopropylcarbamoyloxy)phenyl)propanoate

HRID 449472

반응식

HRID 449472 반응식
[N:1]([CH:4]([CH3:6])[CH3:5])=[C:2]=[O:3].[C:7]([O:11][C:12]([NH:14][C@@H:15]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C>C(Cl)Cl>[C:7]([O:11][C:12]([NH:14][C@@H:15]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:2](=[O:3])[NH:1][CH:4]([CH3:6])[CH3:5])=[CH:23][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])=[O:13])([CH3:10])([CH3:8])[CH3:9]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 7019130Boc-Tyr-OMe

생성물 1

HCID 59496584(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(isopropylcarbamoyloxy)phenyl)propanoate수율 80%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-Isocyanatopropane (Aldrich, Cat. #141070) (22 mg, 0.25 mmol) was added to a solution of methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoate (50 mg, 0.2 mmol) and triethylamine (26 mg, 0.25 mmol) in methylene chloride (2 mL). The reaction was stirred for 1 h. The reaction was partitioned between water and ethyl acetate. The organic phase was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give crude product, (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(isopropylcarbamoyloxy)phenyl)propanoate (50 mg, 80%) as a white solid. Analytical LCMS (M+H-Boc)+: m/z=281.0.

후처리

  1. customThe reaction was partitioned between water and ethyl acetate
  2. washThe organic phase was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e79e9a3b3f1a4e6a875c3838f7851f09
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481732B2

연결된 노트

불러오는 중…