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

HRID 2260153

反応式

HRID 2260153 の反応式
[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]

参加物

4

反応物 1

HCID 75172N-alpha-Benzyloxycarbonyl-L-lysine

生成物 1

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

試薬・触媒・溶媒 2

HCID 10908tert-Butyl acetate溶媒HCID 24247Perchloric Acid溶媒

実験手順

Nα -(Benzyl-oxycarbonyl)-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).

後処理

  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

出典と根拠

ORDレコード
ord-d7e84446f8ea42faac5ebbba8520c894
出典データセット
uspto-grants-1995_12
特許番号
US05476871

関連ノート

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