Methanol → HCID 57518500, compound

HRID 38463Notes

Reaction equation

HRID 38463 reaction equation
[OH-].[Na+:2].[C:3]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[C:14]3[C:48](=[CH:49][CH:50]=2)[O:47][C:17]2([CH2:22][CH2:21][N:20]([C:23]([C:25]4[CH:30]=[C:29]([O:31][CH2:32][CH3:33])[C:28]([C:34]5[CH:39]=[CH:38][C:37]([C:40]([O:42]C)=[O:41])=[CH:36][CH:35]=5)=[C:27]([O:44][CH2:45][CH3:46])[CH:26]=4)=[O:24])[CH2:19][CH2:18]2)[CH2:16][C:15]3=[O:51])=[N:10][CH:11]=1)(=[O:5])[NH2:4].CO>C1COCC1.O>[C:3]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[C:14]3[C:48](=[CH:49][CH:50]=2)[O:47][C:17]2([CH2:22][CH2:21][N:20]([C:23]([C:25]4[CH:26]=[C:27]([O:44][CH2:45][CH3:46])[C:28]([C:34]5[CH:39]=[CH:38][C:37]([C:40]([O-:42])=[O:41])=[CH:36][CH:35]=5)=[C:29]([O:31][CH2:32][CH3:33])[CH:30]=4)=[O:24])[CH2:19][CH2:18]2)[CH2:16][C:15]3=[O:51])=[N:10][CH:11]=1)(=[O:5])[NH2:4].[Na+:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57518501HCID 57518501, compound

Product 1

HCID 57518500HCID 57518500, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous 1N NaOH (11.6 ml, 11.6 mmol) was added to a stirred solution of methyl 4′-({6-(5-carbamoylpyridin-2-yl)-4-oxospiro[chroman-2,4′-piperidin]-1′-yl}carbonyl)-2′,6′-diethoxybiphenyl-4-carboxylate (3.85 g, 5.80 mmol) in THF (40 ml)-MeOH (40 ml) and the mixture was stirred at room temperature for 12 days. After water was added to the mixture, the organic solvents were evaporated under reduced pressure. The aqueous residue was purified by ODS column chromatography eluting with H2O/MeOH and the residue was crystallized from MeOH to give intended compound as a pale red solid. The solid was diluted in H2O and aqueous 1N NaOH, and was purified by ODS column chromatography eluting with H2O/MeOH, and the residue was crystallized from MeOH to give intended compound (2.04 g, 3.04 mmol, 52.4% yield) as a pale red crystal.

Workup

  1. customthe organic solvents were evaporated under reduced pressure
  2. customThe aqueous residue was purified by ODS column chromatography
  3. washeluting with H2O/MeOH
  4. customthe residue was crystallized from MeOH
  5. customto give
  6. customaqueous 1N NaOH, and was purified by ODS column chromatography
  7. washeluting with H2O/MeOH
  8. customthe residue was crystallized from MeOH

Sources & evidence

ORD record
ord-bd79c9ea186848ac9004f8da1dcfa209
Source dataset
uspto-grants-2013_09
Patent number
US08524730B2

Reaction notes

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