Methanol → 81016-66-2

HRID 1378735Notes

Reaction equation

HRID 1378735 reaction equation
C[O:2][C:3](=O)[C:4]([CH3:17])([CH3:16])[NH:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[N+:13]([O-])=O.C([O-])(=O)C.[Na+].CO>[Cl-].[Cl-].[Cl-].[Ti+3].O>[Cl:12][C:10]1[CH:11]=[C:6]2[C:7](=[CH:8][CH:9]=1)[NH:13][C:3](=[O:2])[C:4]([CH3:17])([CH3:16])[NH:5]2

Participants

6

Reactant 3

HCID 887MethanolHCID 517045Sodium AcetateHCID 10707376HCID 10707376, compound

Product 1

HCID 1053646081016-66-2

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 962WaterSolvent

Procedure

Aqueous titanium trichloride (20%, 260 ml) is added dropwise over 10 min to a mixture of N-(5-chloro-2-nitrophenyl)-2-methylalanine methyl ester, (XI, EXAMPLE 11, 14.1 g), sodium acetate (240 g), methanol (504 ml) and water (156 ml). The mixture is stirred for 2.5 hr at 20°-25°. The material is partitioned between aqueous sodium bicarbonate and ethyl acetate, the phases are separated, the organic phase is dried over magnesium sulfate and concentrated under reduced pressure with heat to give the title compound, mp 166°-170°; IR (mineral oil) 3311, 2964, 2954, 2925, 1658, 1614, 1505, 1404 and 1355 cm-1 ; NMR (CDCl3) 8.67, 6.73, 6.6-6.7, 3.78 and 1.42 δ; MS (FAB) m/z 210, 195 and 167.

Workup

  1. customThe material is partitioned between aqueous sodium bicarbonate and ethyl acetate
  2. customthe phases are separated
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. temperaturewith heat

Sources & evidence

ORD record
ord-c47d6089168e4fff8fb601df3cf15662
Source dataset
uspto-grants-1997_09
Patent number
US05668282

Reaction notes

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