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PyBOP → N-Boc-4-iodo-L-phenylalanine ethyl ester

HRID 556392
ノート
印刷プレビュー

反応式

HRID 556392 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)C[CH2:22]1.F[P-](F)(F)(F)(F)F>CCO.CN(C1C=CN=CC=1)C>[CH2:21]([O:11][C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=1)[CH3:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 2724699PyBOPHCID 2755956(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-iodophenyl)propanoic acid

生成物 1

HCID 66909227N-Boc-4-iodo-L-phenylalanine ethyl ester収率 93.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 702Ethanol溶媒

実験手順

To a solution of (S)-2-tert-butoxycarbonylamino-3-(4-iodo-phenyl)-propionic acid (3 g) in anh. EtOH (38 mL) was added DMAP (187 mg) and PyBOP (6 g). The reaction mixture was stirred on at RT and partitioned between EA and water. The org. phase was separated, washed with 10% aq. citric acid and sat. aq. NaHCO3, dried (Na2SO4) and evaporated off. The resulting crude material was purified by CC (Hept/EA 1/0 to 0/1) to afford the title compound as a white solid (3 g).

後処理

  1. custompartitioned between EA and water
  2. customphase was separated
  3. washwashed with 10% aq. citric acid and sat. aq. NaHCO3
  4. dry with materialdried (Na2SO4)
  5. customevaporated off
  6. customThe resulting crude material was purified by CC (Hept/EA 1/0 to 0/1)

出典と根拠

ORDレコード
ord-1273e2f94a5c4e9180889ab29544f177
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08058263B2

反応ノート

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