Acetic Anhydride → Acetic Acid 2-(4-tert-butoxycarbonylamino-2,6-dichloro-phenoxy)-ethyl Ester

HRID 990833Notes

Reaction equation

HRID 990833 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][CH2:16][CH2:17][OH:18])=[C:10]([Cl:19])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:1]([O:5][C:6]([NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][CH2:16][CH2:17][O:18][C:21](=[O:23])[CH3:22])=[C:10]([Cl:19])[CH:9]=1)=[O:20])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54068949[3,5-Dichloro-4-(2-hydroxy-ethoxy)-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 54522332Acetic Acid 2-(4-tert-butoxycarbonylamino-2,6-dichloro-phenoxy)-ethyl Ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of [3,5-dichloro-4-(2-hydroxy-ethoxy)-phenyl]-carbamic acid tert-butyl ester (0.85 g) in pyridine (14 mL) is treated with acetic anhydride (1.24 mL) and the mixture is stirred at room temperature for 15 hours. The solvent is removed under reduced pressure and the residue dissolved in ethyl acetate. This solution is then washed twice with 5% aqueous hydrochloric acid, once with saturated aqueous sodium bicarbonate, and then with saturated aqueous sodium chloride. The solution is dried over anhydrous magnesium sulfate and the solvent is removed under reduced pressure to provide the desired product as a colorless oil.

Workup

  1. customThe solvent is removed under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThis solution is then washed twice with 5% aqueous hydrochloric acid, once with saturated aqueous sodium bicarbonate
  4. dry with materialThe solution is dried over anhydrous magnesium sulfate
  5. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-24353cfdd57845d2833cc8a3a2405d1f
Source dataset
uspto-grants-2002_10
Patent number
US06462055B2

Reaction notes

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