4-(4-(2-Amino-2-methylpropyl)phenoxy)benzamide → (S)-4-(4-[2-(N-[3-(2-amino-3-nitrophenoxy)-2-hydroxypropyl]amino)-2-methylpropyl]phenoxy)benzamide

HRID 1585793Notes

Reaction equation

HRID 1585793 reaction equation
[NH2:1][C:2]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C@H:6]1[O:8][CH2:7]1.[NH2:16][C:17]([CH3:36])([CH3:35])[CH2:18][C:19]1[CH:34]=[CH:33][C:22]([O:23][C:24]2[CH:32]=[CH:31][C:27]([C:28]([NH2:30])=[O:29])=[CH:26][CH:25]=2)=[CH:21][CH:20]=1>C(O)C>[NH2:1][C:2]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C@@H:6]([OH:8])[CH2:7][NH:16][C:17]([CH3:36])([CH3:35])[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:23][C:24]2[CH:32]=[CH:31][C:27]([C:28]([NH2:30])=[O:29])=[CH:26][CH:25]=2)=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 118329614-(4-(2-Amino-2-methylpropyl)phenoxy)benzamideHCID 15049327(S)-3-(2-Amino-3-nitrophenoxy)-1,2-epoxypropane

Product 1

HCID 54045428(S)-4-(4-[2-(N-[3-(2-amino-3-nitrophenoxy)-2-hydroxypropyl]amino)-2-methylpropyl]phenoxy)benzamideYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

A suspension of (S)-3-(2-amino-3-nitrophenoxy)-1,2-epoxypropane (5 g, 23.8 mmol) and 4-(4-(2-amino-2-methylpropyl)phenoxy)benzamide (20.3 g 71.1 mmol) in absolute ethanol (200 mL) was heated to 55° C. for 12 h. All solids went into solution at 50° C. upon completion of the reaction, the solvent was evaporated to dryness. The residue was redissolved in ethyl acetate and washed with a saturated solution of sodium bicarbonate. The layers were separated and the aqueous phase was extracted with ethyl acetate. The two organic layers were combined and washed with brine. The phases were separated and the organic layer was dried over sodium sulfate, filtered, and the solvent evaporated. Column chromatography eluting with 20% MeOH/CHCl3 gave 7.26 g (62%) of product. NMR. MS.

Workup

  1. customAll solids went into solution at 50° C. upon completion of the reaction
  2. customthe solvent was evaporated to dryness
  3. dissolutionThe residue was redissolved in ethyl acetate
  4. washwashed with a saturated solution of sodium bicarbonate
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with ethyl acetate
  7. washwashed with brine
  8. customThe phases were separated
  9. dry with materialthe organic layer was dried over sodium sulfate
  10. filtrationfiltered
  11. customthe solvent evaporated
  12. washColumn chromatography eluting with 20% MeOH/CHCl3

Sources & evidence

ORD record
ord-c6f16ce819c14516a957721a1a2defbd
Source dataset
uspto-grants-1999_08
Patent number
US05939443

Reaction notes

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