Sodium Carbonate → HCID 57663762, compound

HRID 550997Notes

Reaction equation

HRID 550997 reaction equation
[NH2:1][CH2:2][C:3]([O:5][CH3:6])=[O:4].Cl[C:8]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].C([O-])([O-])=O.[Na+].[Na+]>C(O)(C)(C)C>[C:10]([C:9]1[C:8]([NH:1][CH2:2][C:3]([O:5][CH3:6])=[O:4])=[C:16]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:14][CH:13]=1)([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 198702-Chloro-3-nitrobenzoic acidHCID 69221Glycine methyl ester

Product 1

HCID 57663762HCID 57663762, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of methyl glycinate (15.9 g, 127 mmol), 2-chloro-3-nitrobenzoic acid (6.07 g, 30.1 mmol) and Na2CO3 (22.9 g, 216 mmol) in tert-BuOH (40 mL) was heated at reflux for 18 h. The cooled mixture was concentrated under reduced pressure and the residue was partitioned between saturated aqueous H2O (200 mL) and EtOAc (200 mL). The aqueous layer was acidified to pH 2 and the organic layer was extracted. The aqueous layer was extracted further with EtOAc (2×200 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound in sufficient purity for use in the next step. MS: m/z=255 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. concentrationThe cooled mixture was concentrated under reduced pressure
  4. customthe residue was partitioned between saturated aqueous H2O (200 mL) and EtOAc (200 mL)
  5. extractionthe organic layer was extracted
  6. extractionThe aqueous layer was extracted further with EtOAc (2×200 mL)
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b73ea367f10a4f7fb80985f4f143171d
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

Loading…