Sodium Bicarbonate → tert-Butyl 2-methyl-2-[4-({[(4-methyl-1,3-oxazol-5-yl)methyl]amino}methyl)-phenoxy]-propanoate

HRID 353195Notes

Reaction equation

HRID 353195 reaction equation
[CH:1]([C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]([CH3:17])([CH3:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:5][CH:4]=1)=O.[CH3:20][C:21]1[N:22]=[CH:23][O:24][C:25]=1[CH2:26][NH2:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[CH3:16][C:8]([O:7][C:6]1[CH:18]=[CH:19][C:3]([CH2:1][NH:27][CH2:26][C:25]2[O:24][CH:23]=[N:22][C:21]=2[CH3:20])=[CH:4][CH:5]=1)([CH3:17])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22708193tert-Butyl 2-(4-formylphenoxy)-2-methylpropanoateHCID 22708194(4-Methyl-1,3-oxazol-5-yl)methylamine

Product 1

HCID 22708253tert-Butyl 2-methyl-2-[4-({[(4-methyl-1,3-oxazol-5-yl)methyl]amino}methyl)-phenoxy]-propanoate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1.25 g (4.73 mmol) of tert-butyl 2-(4-formylphenoxy)-2-methylpropanoate (Example I-4) and 0.64 g (5.67 mmol) of (4-methyl-1,3-oxazol-5-yl)methylamine (Example III-28) are together initially charged in 1,2-dichloroethane. At room temperature, 1.50 g (7.09 mmol) of sodium triacetoxyborohydride are added. The reaction mixture is stirred at room temperature for 4 hours and then admixed with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulphate and freed from the solvent under reduced pressure. The residue is purified chromatographically on silica gel (dichloromethane/methanol 30:1) and then dried under reduced pressure. This gives 1.104 g (65% of theory) of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. customThe residue is purified chromatographically on silica gel (dichloromethane/methanol 30:1)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-15aa678edc724d93a93c78d1067b1645
Source dataset
uspto-grants-2004_06
Patent number
US06750236B2

Reaction notes

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