Water → HCID 57062129, compound

HRID 278633Notes

Reaction equation

HRID 278633 reaction equation
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]

Participants

6

Reactant 4

HCID 962WaterHCID 516920Potassium bisulfateHCID 18648793HCID 18648793, compoundHCID 85633486HCID 85633486, compound

Product 1

HCID 57062129HCID 57062129, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%);

Workup

  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.)

Sources & evidence

ORD record
ord-a2ea539c411d4667b80fbd5c9abb5e00
Source dataset
uspto-grants-2002_03
Patent number
US06359113B1

Reaction notes

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