Benzyl chloroformate → Boc-dap(Z)-OH

HRID 1504818노트

반응식

HRID 1504818 반응식
[NH2:1][CH2:2][C@@H:3]([C:12]([OH:14])=[O:13])[NH:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[OH-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C1COCC1.O>[CH2:27]([O:26][C:24]([NH:1][CH2:2][C@@H:3]([C:12]([OH:14])=[O:13])[NH:4][C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6])=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

7

반응물 4

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 2755946Boc-Dap-OH

생성물 1

HCID 2755950Boc-dap(Z)-OH

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of 3-amino-N-(tert-butoxycarbonyl)alanine (5.0 g, 25 mmol), potassium hydroxide (1.6 g, 29 mmol) and potassium carbonate (6.9 g, 29 mmol) in THF (60 mL) and water (20 mL) was added dropwise benzyl chloroformate (5.0 g, 29 mmol) at 0° C. The reaction mixture was allowed to warm to ambient temperature. After 16 hours, the reaction mixture was concentrated under reduced pressure, and the residue was washed with water followed by petroleum ether to afford 3-{[(benzyloxy)carbonyl]amino}-N-(tert-butoxycarbonyl)alanine. MS ESI calc'd. for C16H23N2O6 [M+H]+ 339. found 339. 1H NMR (300 MHz, CD3OD) δ 7.33-7.26 (m, 5H), 5.03 (s, 2H), 4.03-4.01 (m, 1H), 3.49-3.35 (m, 2H), 1.44 (s, 9H).

후처리

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. washthe residue was washed with water

출처 및 근거

ORD 기록
ord-0e00d8a05e404b75a216457608dced05
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216173B2

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