Acetic Acid → N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-iodo-L-phenylalanine

HRID 403007노트

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HRID 403007 반응식
C([O:3][C:4](=[O:38])[C@H:5]([CH2:14][C:15]1[C:20]([I:21])=[CH:19][C:18]([O:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[C:17]([O:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:16]=1)[NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])C.[OH-].[Li+].C(O)(=O)C>C1COCC1.O>[C:10]([O:9][C:7]([NH:6][C@H:5]([C:4]([OH:38])=[O:3])[CH2:14][C:15]1[C:20]([I:21])=[CH:19][C:18]([O:22][C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])=[C:17]([O:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:16]=1)=[O:8])([CH3:11])([CH3:12])[CH3:13]

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 10651861N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-iodo-L-phenylalanine ethyl ester

생성물 1

HCID 66733684N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-iodo-L-phenylalanine

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

The iodo derivative 17 (3.5 mmol) (prepared as shown in FIG. 6) was dissolved in 40 mL of THF and cooled in an ice bath (0° C.) and a solution of lithium hydroxide (7.0 mmol) in 12 mL of water was added dropwise under argon. The resulting mixture was stirred at 0° C. for 4 h and then 2 h at room temperature. The reaction mixture was then neutralized with acetic acid to pH 5 and extracted with ethyl acetate. The organic phase was dried using Na2SO4, filtered and evaporated to dryness to provide an oil which was purified by silical gel column chromatography resulting in N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-iodo-L-phenylalanine (23).

후처리

  1. custom2 h
  2. customat room temperature
  3. extractionextracted with ethyl acetate
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customto provide an oil which
  8. customwas purified by silical gel column chromatography
  9. customresulting in N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-iodo-L-phenylalanine (23)

출처 및 근거

ORD 기록
ord-e3264ddc1553450cb2aa5d82cebe6799
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742139B2

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