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

HRID 1456646ノート

反応式

HRID 1456646 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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##

後処理

  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

出典と根拠

ORDレコード
ord-59491923daae41ca8b468306e888c426
出典データセット
uspto-grants-1998_12
特許番号
US05843904

反応ノート

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