Pivaloyl chloride → Ethyl N-benzyl-N-((tert-butoxycarbonyl)-L-valyl)glycinate

HRID 1456646노트

반응식

HRID 1456646 반응식
[C:1]([NH:8][C@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(C(C)C)C(C)C.CC(C)(C)C(Cl)=O.[CH2:32]([O:34][C:35](=[O:45])[CH2:36][NH:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:33]>C(Cl)Cl>[CH2:32]([O:34][C:35](=[O:45])[CH2:36][N:37]([C:13](=[O:15])[C@@H:9]([NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH:10]([CH3:11])[CH3:12])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:33]

참가 물질

6

반응물 4

HCID 62493Pivaloyl chlorideHCID 80908N-Benzylglycine ethyl esterHCID 81531DiisopropylethylamineHCID 83693Boc-L-Valine

생성물 1

HCID 23402347Ethyl N-benzyl-N-((tert-butoxycarbonyl)-L-valyl)glycinate수율 87.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of N-Boc-valine (2.18 g, 10 mmol) and DIEA (4.4 mL, 25.3 mmol) in CH2Cl2 (20 mL) at -20° C. was added trimethylacetyl chloride (1.2 mL, 9.7 mmol). After stirring for 30 min, compound 701 (2.18 g, 10 mmol) was added and the reaction allowed to warm to rt and stir for 5 hr. The reaction was concentrated in vacuo and the residue taken up into EtOAc and H2O. The layers were separated and the organic phase washed with sat. aq. NaHCO3, sat. aq. KHSO4, brine, dried over MgSO4, filtered and concentrated in vacuo to provide 3.45 g of compound 702. ##STR81##

후처리

  1. stirringstir for 5 hr
  2. concentrationThe reaction was concentrated in vacuo
  3. customThe layers were separated
  4. washthe organic phase washed with sat. aq. NaHCO3, sat. aq. KHSO4, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-59491923daae41ca8b468306e888c426
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05843904

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