Dichloromethane → HCID 70435137, compound

HRID 2308693Notes

Reaction equation

HRID 2308693 reaction equation
[CH:1]1([N:7]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:8](=[O:24])[CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([CH:22]=[O:23])[CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(OCC)(=[O:32])C.S(=O)(O)[O-].[Na+].ClCCl>N1C=CC=CC=1>[CH:1]1([N:7]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:8](=[O:24])[CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([C:22]([OH:32])=[O:23])[CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 13756717HCID 13756717, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 70435137HCID 70435137, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl 2-(N-cyclohexyl-4-(3-formyl-4-nitrophenyl)oxybutyramidyl)acetate (3.5 g) in dry pyridine (20 ml) under a blanket of nitrogen was added solid tetra-N-butylammonium permanganate portionwise over 1 hour. The reaction was stirred at room temperature for 1 hour and was then poured into ethyl acetate/6M hydrogen chloride (100 ml each). Solid sodium bisulfite was added to decolorize the solution and the layers were separated. The aqueous layer was washed with ethyl acetate (2×50 ml). The combined organic layers were washed with 1M HCl (3×50 ml) and brine (2×50 ml), dried, filtered and evaporated to give a syrup which foamed at high vacuum from dichloromethane to yield methyl 2-(N-cyclohexyl-4-(3-carboxy-4-nitrophenyl)oxybutyramidyl)acetate.

Workup

  1. customthe layers were separated
  2. washThe aqueous layer was washed with ethyl acetate (2×50 ml)
  3. washThe combined organic layers were washed with 1M HCl (3×50 ml) and brine (2×50 ml)
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto give a syrup which

Sources & evidence

ORD record
ord-6e9cb13b10b44c1c90486e91c6e86233
Source dataset
uspto-grants-1987_09
Patent number
US04690925

Reaction notes

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