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

HRID 403007ノート

反応式

HRID 403007 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e3264ddc1553450cb2aa5d82cebe6799
出典データセット
uspto-grants-2014_06
特許番号
US08742139B2

反応ノート

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