Citric Acid → HCID 69419080, compound

HRID 1292748Notes

Reaction equation

HRID 1292748 reaction equation
C[O-].[Na+].[CH3:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([O:12][C@@H:13]([C@@:17]2([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[NH:23][CH2:22][C:21](=[O:24])[N:20]([CH3:25])[C:19]3[CH:26]=[CH:27][CH:28]=[CH:29][C:18]2=3)[C:14]([OH:16])=[O:15])[N:6]=1.[C:36](O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O>[CH3:36][O:15][C:14](=[O:16])[C@@H:13]([O:12][C:7]1[N:6]=[C:5]([CH3:4])[CH:10]=[C:9]([CH3:11])[N:8]=1)[C@@:17]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:23][CH2:22][C:21](=[O:24])[N:20]([CH3:25])[C:19]2[CH:26]=[CH:27][CH:28]=[CH:29][C:18]1=2

Participants

6

Reactant 3

HCID 311Citric AcidHCID 10224745HCID 10224745, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 69419080HCID 69419080, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium methylate (10.14 g, 186 mmol) is added at 0° C. to a solution of (±)-(1S*, 9bS*)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-methyl-9b-phenyl-5,9b-dihydro-1H-2a,5-diaza-benzo[a]cyclobuta[c]cycloheptene-2,4-dione (5.0 g, 12 mmol, Example 49) in methanol (250 ml). The solution is stirred at rt for 3 h, poured into a solution of citric acid (12.6 g, mono hydrate) in water (600 ml) and extracted three times with EA. The organic phase is washed with brine, dried over MgSO4 and evaporated to give (±)-(S*)-(4,6-dimethyl-pyrimidin-2-yloxy)-((5S*)-1-methyl-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl)-acetic acid methyl ester (5.04 g) as a white foam. LC-MS1: tR=0.94 min, [M+1]+=447.07.

Workup

  1. extractionextracted three times with EA
  2. washThe organic phase is washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-9f17511e4e164fa3964e8b659e36e9dd
Source dataset
uspto-grants-2007_07
Patent number
US07238685B2

Reaction notes

Loading…