Water → HCID 15335301, compound

HRID 248293Notes

Reaction equation

HRID 248293 reaction equation
CC([NH:5][S:6]([C:9]1[C:14]([S:15]([CH2:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1)(=[O:8])=[O:7])(C)C.ClC1C=CC=C(C(OO)=[O:28])C=1.O>C(Cl)Cl.FC(F)(F)C(O)=O>[CH2:17]([S:15]([C:14]1[C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[N:10][CH:11]=[CH:12][CH:13]=1)(=[O:16])=[O:28])[CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 15335300HCID 15335300, compound

Product 1

HCID 15335301HCID 15335301, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred solution of 8.8 g (0.029 mol) of the product from Example 3 in 400 mls methylene chloride cooled to -5°, under nitrogen, was added 6.6 g (0.038 mol) of 3-chloroperbenzoic acid and stirred at room temperature for 20 hours. The reaction mixture was poured into water and extracted with methylene chloride. The organic layers were combined and washed with saturated sodium bisulfite and brine, dried over magnesium sulfate, and evaporated to a solid mixture which was washed with hexanes to afford a white solid. The solid was dissolved and stirred in 150 mls trifluoroacetic acid for 72 hours. The solution was evaporated and triturated with ether to afford 5.3 g (46%) white solid: m.p. 153°-157°; NMR (CDCl3, 200 MHz) 1.06 (3H, t, J=7 Hz), 1.8 (2H, m), 3.7 (2H, m) 5.8 (NH2), 7.8 (1H, m), 8.6 (1H, m), 8.95 (1H, m); IR (nujol) 3390, 3180, 1360, 1310, 1175, 1150 cm-1.

Workup

  1. extractionextracted with methylene chloride
  2. washwashed with saturated sodium bisulfite and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to a solid mixture which
  5. washwas washed with hexanes
  6. customto afford a white solid
  7. dissolutionThe solid was dissolved
  8. customThe solution was evaporated
  9. customtriturated with ether

Sources & evidence

ORD record
ord-3b9e6680700548f8b9623fc5543be726
Source dataset
uspto-grants-1993_05
Patent number
US05209770

Reaction notes

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