Water → HCID 57062129、化合物

HRID 278633ノート

反応式

HRID 278633 の反応式
C(=O)([O-])OC1C=CC([N+]([O-])=O)=CC=1[CH2:12][CH:13]1[C:25]2[C:20](=[C:21]3[CH:33]=[CH:32][CH:31]=[CH:30][C:22]3=[C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]3=2)[C:19]2[C:14]1=[C:15]1[CH:41]=[CH:40][CH:39]=[CH:38][C:16]1=[C:17]1[CH:37]=[CH:36][CH:35]=[CH:34][C:18]1=2.[C:44]([OH:47])(=[O:46])C.[C:48]([O:52][C:53](=[O:63])[C@H:54]([CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[NH2:55])([CH3:51])([CH3:50])[CH3:49].O.OS([O-])(=O)=O.[K+]>ClCCl>[C:48]([O:52][C:53](=[O:63])[C@H:54]([CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[NH:55][C:44]([O:47][CH2:12][CH:13]1[C:14]2[C:19](=[C:18]3[CH:34]=[CH:35][CH:36]=[CH:37][C:17]3=[C:16]3[CH:38]=[CH:39][CH:40]=[CH:41][C:15]3=2)[C:20]2[C:25]1=[C:24]1[CH:26]=[CH:27][CH:28]=[CH:29][C:23]1=[C:22]1[CH:30]=[CH:31][CH:32]=[CH:33][C:21]1=2)=[O:46])([CH3:51])([CH3:49])[CH3:50]

参加物

6

反応物 4

HCID 962WaterHCID 516920Potassium bisulfateHCID 18648793HCID 18648793、化合物HCID 85633486HCID 85633486、化合物

生成物 1

HCID 57062129HCID 57062129、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 17-tetrabenzo(a,c,g,i)fluorenylmethyl-para-nitrophenyl carbonate (139.4 mg, 0.248 mmol) and L-phenylalanine tert-butyl ester acetate (83.9 mg, 0.298 mmol; 1.2 equiv) in dichloromethane (5 ml) was added N,N′-dimethylaniline (63 μl, 0.497 mmol; 2 equiv). The reaction mixture was stirred at room temperature under nitrogen for 120 h. After addition of water (10 ml) and acidification with KHSO4 (2M) to pH=1, the reaction mixture was extracted with dichloromethane (3×20 ml). The combined organic phases were washed with water (2×15 ml) to pH 6-7 and dried over MgSO4. After filtration the solvent was evaporated under reduced pressure to give an orange oil. After purification by flash chromatography using toluene as the eluent, the fractions containing material of Rf=0.04 were evaporated to give a yellow solid. Recrystallization from ether/petrol (b.p. 40-60° C.) gave compound (54) as a pale yellow solid which was filtered, washed with petrol and finally dried (73.9 mg, 46%);

後処理

  1. extractionthe reaction mixture was extracted with dichloromethane (3×20 ml)
  2. washThe combined organic phases were washed with water (2×15 ml) to pH 6-7
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration the solvent
  5. customwas evaporated under reduced pressure
  6. customto give an orange oil
  7. customAfter purification by flash chromatography
  8. additionthe fractions containing material of Rf=0.04
  9. customwere evaporated
  10. customto give a yellow solid
  11. customRecrystallization from ether/petrol (b.p. 40-60° C.)

出典と根拠

ORDレコード
ord-a2ea539c411d4667b80fbd5c9abb5e00
出典データセット
uspto-grants-2002_03
特許番号
US06359113B1

反応ノート

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