Methanol → HCID 13630983, compound

HRID 1981534Notes

Reaction equation

HRID 1981534 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:27])=[C:5]([C:23]([O:25][CH3:26])=[O:24])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:18][O:19]C(=O)C)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].CO.C(=O)([O-])[O-].[K+].[K+]>CCOCC>[CH3:1][C:2]1[NH:3][C:4]([CH3:27])=[C:5]([C:23]([O:25][CH3:26])=[O:24])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:18][OH:19])[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 13630981HCID 13630981, compound

Product 1

HCID 13630983HCID 13630983, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 100 ml round bottomed flask with a magnetic stirring bar was added the compound (1d) (1.27 g, 3.40 mmol) methanol (50 ml), and powdered anhydrous potassium carbonate (14 mg, 1 mmol). The mixture was stirred for 5 hours at room temperature. The reaction mixture was then diluted with ether (200 ml) and was washed with water (2×75 ml) and brine (1×100 ml). Drying (MgSO4), filtration and removal of the solvent in vacuo. Recrystallization of the residue from boiling ethyl acetate-hexanes gave the compound (1e) as white crystals: mp 218°-220° C. 'H NMR (CDCl3) δ2.25 (s, 6H), 3.55 (s, 6H), 4.35 (br d, 1H, J=6 Hz), 4.85 (d, 2H, J=6 Hz), 5.13 (s, 1H), 5.93 (br s, 1H), 7.00-7.40 (m, 4H). Anal. Calcd. for C18H21NO5 : C, 65.24; H, 6.39; N, 4.23. Found: C, 65.44; H, 6.41; N, 4.41.

Workup

  1. washwas washed with water (2×75 ml) and brine (1×100 ml)
  2. customDrying
  3. filtration(MgSO4), filtration and removal of the solvent in vacuo
  4. customRecrystallization of the residue

Sources & evidence

ORD record
ord-49c52268748a4a0680b23d59fcee88bc
Source dataset
uspto-grants-1986_06
Patent number
US04593033

Reaction notes

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