Water → HCID 57062129, 화합물

HRID 278633노트

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HRID 278633 반응식
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]

참가 물질

6

반응물 4

HCID 962WaterHCID 516920Potassium bisulfateHCID 18648793HCID 18648793, 화합물HCID 85633486HCID 85633486, 화합물

생성물 1

HCID 57062129HCID 57062129, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%);

후처리

  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.)

출처 및 근거

ORD 기록
ord-a2ea539c411d4667b80fbd5c9abb5e00
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06359113B1

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