N-alpha-Benzyloxycarbonyl-L-lysine → N2-[(Phenylmethoxy)carbonyl]-L-lysine tert-Butyl Ester

HRID 21743

반응식

HRID 21743 반응식
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OC(C)(C)C)(=O)C.Cl(O)(=O)(=O)=O>[C:2]([O:19][C:18](=[O:20])[C@H:12]([CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])([CH3:7])([CH3:3])[CH3:1]

참가 물질

4

반응물 1

HCID 75172N-alpha-Benzyloxycarbonyl-L-lysine

생성물 1

HCID 11078219N2-[(Phenylmethoxy)carbonyl]-L-lysine tert-Butyl Ester수율 72%

시약·촉매·용매 2

HCID 10908tert-Butyl acetate용매HCID 24247Perchloric Acid용매

실험 절차

Nα -(Benzyloxycarbonyl)-L-lysine (5.0 gm, 17.84 mmol) was dissolved in 268 ml of tert-butyl acetate containing 2.80 ml of perchloric acid (69-72% aqueous solution). The solution was stirred for 2 days at room temperature and then was extracted with water (3×200 ml). The combined aqueous layers were adjusted to pH 10 with 50% sodium hydroxide. The aqueous solution was then extracted with ethyl acetate (3×200 ml) and the organic layers dried over MgSO4. After filtration to remove MgSO4, the solvent was removed by evaporation at reduced pressure to provide Nα -(benzyloxycarbonyl)-L-lysine tert-butyl ester as a clear oil (2.16 gm, 36%). 1H NMR (CDCl3) 1.35 (s,9H), 1.40-2.0 (m,6H), 2.60 (t,2H), 4.10 (m, 1H), 4.98 (s,2H), 5.29 (bs,1H), 7.35 (s,5H).

후처리

  1. extractionwas extracted with water (3×200 ml)
  2. extractionThe aqueous solution was then extracted with ethyl acetate (3×200 ml)
  3. dry with materialthe organic layers dried over MgSO4
  4. filtrationAfter filtration
  5. customto remove MgSO4
  6. customthe solvent was removed by evaporation at reduced pressure

출처 및 근거

ORD 기록
ord-8224666d4e8f467c8cbd4d16ff05bd05
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424447

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