Sodium Methoxide → HCID 14751595, compound

HRID 1650143Notes

Reaction equation

HRID 1650143 reaction equation
C(OC([O:11][C:12]1[C:21]2[C:16](=[C:17]([CH2:33][N:34]([C:41]([O:43][CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)=[O:42])[CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[C:18]([O:22]C(OCC3C=CC=CC=3)=O)=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[CH2:51][N:52]([C:59]([O:61][CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)=[O:60])[CH:53]1[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]1)=O)C1C=CC=CC=1.C[O-].[Na+]>CO>[OH:11][C:12]1[C:21]2[C:16](=[C:17]([CH2:33][N:34]([C:41]([O:43][CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)=[O:42])[CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[C:18]([OH:22])=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[CH2:51][N:52]([C:59]([O:61][CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)=[O:60])[CH:53]1[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 14751594HCID 14751594, compound

Product 1

HCID 14751595HCID 14751595, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the crude product from Step B (2.0 g, 2.3 mmol) in methanol (50 ml) was treated with sodium methoxide (120 mg, 2.2 mmol) for 18 hours at room temperature. The mixture was evaporated, the residue taken up in diethyl ether, acetic acid (1 ml) added, the solution washed three times with water, saturated aqueous sodium chloride solution, dried (sodium sulfate) and evaporated. The crude product was vacuum filtered through a column of silica gel (Merck #7734) eluted with 2:1 hexane-ether; yield 1.5 g.

Workup

  1. customThe mixture was evaporated
  2. additionacetic acid (1 ml) added
  3. washthe solution washed three times with water, saturated aqueous sodium chloride solution
  4. dry with materialdried (sodium sulfate)
  5. customevaporated
  6. filtrationfiltered through a column of silica gel (Merck #7734)
  7. washeluted with 2:1 hexane-ether

Sources & evidence

ORD record
ord-c5bb82ec720b46c08b67b81711ee6d0e
Source dataset
uspto-grants-1990_05
Patent number
US04923852

Reaction notes

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