Ammonia → 2-(3,5-Di-t-butyl-4-hydroxyphenyl)-4-(2-(4-methylethylaminomethylphenoxy) ethyl)-5-methyloxazole hydrochloride hydrate

HRID 618523Notes

Reaction equation

HRID 618523 reaction equation
[CH3:1][NH:2][CH2:3][CH3:4].[C:5]([C:9]1[CH:10]=[C:11]([C:20]2[O:21][C:22]([CH3:36])=[C:23]([CH2:25][CH2:26][O:27][C:28]3[CH:33]=[CH:32][C:31]([CH:34]=O)=[CH:30][CH:29]=3)[N:24]=2)[CH:12]=[C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:14]=1[OH:15])([CH3:8])([CH3:7])[CH3:6].[BH4-].[Na+].N.C(Cl)[Cl:41]>C(O)C>[OH2:15].[ClH:41].[C:16]([C:13]1[CH:12]=[C:11]([C:20]2[O:21][C:22]([CH3:36])=[C:23]([CH2:25][CH2:26][O:27][C:28]3[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][C:33]=3[CH2:1][NH:2][CH2:3][CH3:4])[N:24]=2)[CH:10]=[C:9]([C:5]([CH3:6])([CH3:8])[CH3:7])[C:14]=1[OH:15])([CH3:18])([CH3:19])[CH3:17]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 6344DichloromethaneHCID 12219N-MethylethylamineHCID 4311764Sodium borohydrideHCID 1357250662-(3,5-Di-t-butyl-4-hydroxyphenyl)-4-(2-(4-formylphenoxy)ethyl)-5-methyloxazole

Product 1

HCID 1364704832-(3,5-Di-t-butyl-4-hydroxyphenyl)-4-(2-(4-methylethylaminomethylphenoxy) ethyl)-5-methyloxazole hydrochloride hydrateYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methylethylamine, 0.71 ml (8.32 mmole) and 2.46 ml (8.32 mmole) Ti(OPr)4 were dissolved in 17 ml of ethanol and stirred for 10 minutes under nitrogen. Compound of step D, 1.75 g (4.16 mmole), was added and the mixture was stirred for 4 hours. Sodium borohydride, 240 mg (6.23 mmole) was added and the reaction was stirred for 3 days. Ammonia, 5.8 ml 2N, was added to give a thick suspension. Methylene chloride (40 ml) was added then 5.3 g diatomaceous earth and the mixture was stirred, and filtered through diatomaceous earth. The filtrate was washed 2 times with brine then dried. The organics were stripped and chromatographed, eluting with methylene chloride/methanol/concentrated ammonia 90:10:1. Fractions were bulked, stripped, dissolved in methylene chloride/isopropyl ether. Hydrogen chloride gas was bubbled in. Product was evaporate to dryness to give 1.36 g (63%) of a white foam.

Workup

  1. stirringthe mixture was stirred for 4 hours
  2. stirringthe reaction was stirred for 3 days
  3. customto give a thick suspension
  4. stirring5.3 g diatomaceous earth and the mixture was stirred
  5. filtrationfiltered through diatomaceous earth
  6. washThe filtrate was washed 2 times with brine
  7. customthen dried
  8. customchromatographed
  9. washeluting with methylene chloride/methanol/concentrated ammonia 90:10:1
  10. dissolutiondissolved in methylene chloride/isopropyl ether
  11. customHydrogen chloride gas was bubbled in
  12. customProduct was evaporate to dryness

Sources & evidence

ORD record
ord-8ee45614582c4f6798f329e092df2b81
Source dataset
uspto-grants-1999_09
Patent number
US05952360

Reaction notes

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