Acetic Acid → t-Butyl 4-aminophenoxyacetate, acetate salt

HRID 1900878Notes

Reaction equation

HRID 1900878 reaction equation
C(OC([NH:11][C:12]1[CH:26]=[CH:25][C:15]([O:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:14][CH:13]=1)=O)C1C=CC=CC=1.C(O)(=O)C.[H][H]>C(O)C.[Pd]>[C:18]([OH:20])(=[O:19])[CH3:17].[NH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 23370045t-Butyl 4-benzyloxycarbonylaminophenoxyacetateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 131719648t-Butyl 4-aminophenoxyacetate, acetate saltYield 126.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the product of step (b) (5 g) in ethanol (300 ml) containing glacial acetic acid (0.8 ml) under argon was added 10% Pd on C (250 mg). The argon was replaced by hydrogen and the reaction mixture was stirred under a blanket of hydrogen for 4 hours. The catalyst was filtered off through a pad of diatomaceous earth and washed with ethanol, and the combined filtrate and washings were evaporated to dryness to yield t-butyl 4-aminophenoxyacetate, acetate salt (2.5 g) as brown oil: NMR Spectrum (DMSO-d6) 1.41 (9H, s), 1.86 (3H, s), 4.43 (2H, s), 5.12 (2H, s), 6.49 (2H, d), 6.60 (2H, m).

Workup

  1. filtrationThe catalyst was filtered off through a pad of diatomaceous earth
  2. washwashed with ethanol
  3. customthe combined filtrate and washings were evaporated to dryness

Sources & evidence

ORD record
ord-931af615e42e4895a908e08c6793d77e
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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