Hydrochloric Acid → tert-butyl N-(3-hydroxy-2,6-dimethylphenyl)carbamate

HRID 1771635Notes

Reaction equation

HRID 1771635 reaction equation
C(=O)([O-])OC(C)(C)C[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([N:12](C(=O)C)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:6]=1[CH3:23].[OH2:28].NN.Cl>CC(O)(C)C>[OH:28][C:5]1[C:6]([CH3:23])=[C:7]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]([CH3:11])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 131734659[3-(Acetyl(tert-butoxycarbonyl)amino)-2,4-dimethyl-phenyl]tert-butyl carbonate

Product 1

HCID 89443943tert-butyl N-(3-hydroxy-2,6-dimethylphenyl)carbamate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of [3-(acetyl(tert-butoxycarbonyl)amino)-2,4-dimethyl-phenyl]tert-butyl carbonate (800 mg, 2.11 mmol, 1.0 eq) and hydrazine hydrate (5 mL) in t-BuOH (5 mL) was stirred under N2 at 110° C. overnight. The solution was adjusted to pH 6 by addition of diluted HCl and the aqueous layer extracted with EtOAc. The organic extract was dried (Na2SO4), filtered and evaporated in vacuo. The crude solid was used in the next step without further purification (657 mg, 100%).

Workup

  1. extractionthe aqueous layer extracted with EtOAc
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude solid was used in the next step without further purification (657 mg, 100%)

Sources & evidence

ORD record
ord-3b25949fa4294f3d9f8ecb114f9f408e
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

Loading…