Sodium Carbonate → HCID 15297072, compound

HRID 727665Notes

Reaction equation

HRID 727665 reaction equation
[C:1]([C@@H:4]1[CH2:8][C@H:7]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:6][N:5]1[CH3:19])(=[O:3])N.C(=O)([O-])[O-:21].[Na+].[Na+]>Cl>[C:1]([C@@H:4]1[CH2:8][C@H:7]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:6][N:5]1[CH3:19])([OH:21])=[O:3]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 14796652(2S,4S)-2-carbamoyl-4-(4-methoxybenzylthio)-1-methylpyrrolidine

Product 1

HCID 15297072HCID 15297072, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

15.16 g of (2S,4S)-2-carbamoyl-4-(4-methoxybenzylthio)-1-methylpyrrolidine [prepared as described in step (i) above] were dissolved in 170 ml of 2N aqueous hydrochloric acid, and the solution was stirred in a bath kept at 110° C. for 3.5 hours. At the end of this time, the reaction mixture was cooled to room temperature, and its pH was adjusted to a value of by the addition of sodium carbonate. The mixture was then concentrated by evaporation under reduced pressure, after which it was allowed to stand in a refrigerator precipitate crystals. The precipitated crystals were collected by filtration and washed with a small amount of cold water. They were then dried, to give 10.4 g of the title compound. The mother liquor was then concentrated by evaporation under reduced pressure, and the residue was subjected to column chromatography through CHP20P (75-150μ, Mitsubishi Chemical Industries, Ltd.), using 50% v/v aqueous methanol as the eluent, to afford a further 3.7 g of the title compound, as crystals melting an 185°-187.5° C.

Workup

  1. concentrationThe mixture was then concentrated by evaporation under reduced pressure
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with a small amount of cold water
  4. customThey were then dried

Sources & evidence

ORD record
ord-1542c49f339e44e2bae709f01a9391d5
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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