Water → HCID 20029931, compound

HRID 1721984Notes

Reaction equation

HRID 1721984 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:13][CH2:14]NCC(O)CO)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].COC(C1N=[C:27]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH:38]([OH:45])[CH2:39]NC(C)(C)C)=[CH:32][CH:31]=2)NC=1)=O.[OH2:46]>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:13][CH2:14][CH2:39][CH:38]([OH:45])[CH2:37][O:36][C:33]2[CH:34]=[CH:35][C:30]([CH:27]=[O:46])=[CH:31][CH:32]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 12875895HCID 12875895, compoundHCID 178498876HCID 178498876, compound

Product 1

HCID 20029931HCID 20029931, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
120 °C

Procedure

To a suspension of NaH (60% oil dispersion, 1.2 g, 0.03 mol) in DMF (20 ml) was added at 70° C. under N2 a solution 3 (37 g, 0.03 ml) in DMF (30 ml). After stirring for 15 minutes at 70° C. a solution of (S) 2 in DMF (50 ml) was added dropwise. After the addition, the mixture was heated at 120° C. for 18 hours. The solution was then poured into H2O and extracted with EtOAc (3X). The organic extracts were washed with H2O (2X), saturated NaCl (1X), dried, filtered and concentrated to dryness. The residue was treated with H2O (250 ml) and AcOH (25 ml) and stirred overnight at room temperature. The solution was extracted with EtOAc (2X), neutralized with saturated Na2CO3 and extracted with CHCl3 (9X). The organic extracts were dried, filtered and concentrated to yield 8.5 g of 4; 'H NMR (CDCl3) δ 2.7 (6H, m), 3.8 (6H, s), 4.1 (3H, m), 6.7 (3H, bs), 6.95 (2H, d), 7.75 (2H, d). ##STR152##

Workup

  1. additionwas added dropwise
  2. additionAfter the addition
  3. extractionextracted with EtOAc (3X)
  4. washThe organic extracts were washed with H2O (2X), saturated NaCl (1X)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. additionThe residue was treated with H2O (250 ml) and AcOH (25 ml)
  9. extractionThe solution was extracted with EtOAc (2X)
  10. extractionextracted with CHCl3 (9X)
  11. customThe organic extracts were dried
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-045fa589b3474dba9548301fe31d6ee5
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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