Methanol → HCID 67371647, compound

HRID 1254956Notes

Reaction equation

HRID 1254956 reaction equation
[CH3:1]O.CO.C[O-].[Na+].[OH:8][C@H:9]([C@H:24]1[CH2:28][O:27]C(=O)[O:25]1)[C@H:10]1[C@H:15]2[N:16]=[C:17]([CH3:19])[O:18][C@@H:14]2[CH:13]=[C:12]([C:20]([O:22][CH3:23])=[O:21])[O:11]1>C1(C)C=CC=CC=1>[OH:25][C@H:24]([CH2:28][OH:27])[C@H:9]([C@H:10]1[C@H:15]2[N:16]=[C:17]([CH3:19])[O:18][C@@H:14]2[CH:13]=[C:12]([C:20]([O:22][CH3:23])=[O:21])[O:11]1)[O:8][CH3:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 23694274Sodium methanolate methanolHCID 67371627HCID 67371627, compound

Product 1

HCID 67371647HCID 67371647, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Methanol (460 ml) and a 25.4% sodium methoxide methanol solution (14.36 g) were added to a toluene solution (approximately 675 ml) of a compound, which was obtained by subjecting methyl (3aS,4R,7aR)-4-{(S)-hydroxy[(4R)-2-oxo-1,3-dioxolan-4-yl]methyl}-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate (46.00 g) to Step A-5 of Example 1, at room temperature, and the mixture was stirred for 30 minutes at the same temperature. The solvent of the reaction solution was distilled off under reduced pressure until the amount of solution became approximately 138 ml, methanol (460 ml) was added, and the reaction solution was stirred for 30 minutes at room temperature. After acetic acid (4.41 g) was added to the reaction solution and the solvent was distilled off under reduced pressure until the amount of solution became approximately 138 ml, toluene (230 ml) was added to the reaction solution and then the solvent was distilled off again under reduced pressure until the amount of solution became 138 ml to give a toluene suspension of the title compound.

Workup

  1. customwhich was obtained
  2. distillationThe solvent of the reaction solution was distilled off under reduced pressure until the amount of solution
  3. additionwas added
  4. stirringthe reaction solution was stirred for 30 minutes at room temperature
  5. additionAfter acetic acid (4.41 g) was added to the reaction solution
  6. distillationthe solvent was distilled off under reduced pressure until the amount of solution
  7. additionwas added to the reaction solution
  8. distillationthe solvent was distilled off again under reduced pressure until the amount of solution
  9. customto give

Sources & evidence

ORD record
ord-7e6f69b99b7a4b939d642597dfbe8431
Source dataset
uspto-grants-2013_06
Patent number
US08455659B2

Reaction notes

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