Benzyl chloroformate → Benzyl 2-(2-tert-butylphenoxy)pyridin-3-ylcarbamate

HRID 1160234Notes

Reaction equation

HRID 1160234 reaction equation
[C:1]([C:5]1[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=1[O:7][C:8]1[C:13]([N:14]=C=O)=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].CCN(C(C)C)C(C)C.[Cl-].[NH4+]>ClCCl>[C:1]([C:5]1[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=1[O:7][C:8]1[C:13]([NH:14][C:22](=[O:23])[O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 10387Benzyl chloroformateHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 574233152-(2-tert-Butylphenoxy)-3-isocyanatopyridine

Product 1

HCID 67026951Benzyl 2-(2-tert-butylphenoxy)pyridin-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(2-tert-butylphenoxy)pyridin-3-amine (1a) (880 mg, 3.6 mmol), benzyl chloroformate (575 uL, 4.0 mmol) and Hunig's base (935 uL, 5.4 mmol) in dichloromethane (9.0 mL) was stirred at rt for 16 h. Saturated ammonium chloride was added and the separated aqueous layer was extracted with dichloromethane (3×15 mL). The combined organic layers were dried (anh. Magnesium sulfate), filtered and evaporated to yield a residue which was purified by reverse phase preparative HPLC. LC-MS m/z 377.1 [M+H]+.

Workup

  1. extractionthe separated aqueous layer was extracted with dichloromethane (3×15 mL)
  2. dry with materialThe combined organic layers were dried (anh. Magnesium sulfate)
  3. filtrationfiltered
  4. customevaporated
  5. customto yield a residue which
  6. customwas purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-b65b071451824639b459b2397eda3b84
Source dataset
uspto-grants-2010_10
Patent number
US07816382B2

Reaction notes

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