Methanol → HCID 19066090, compound

HRID 481306Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:7]([S:12][C:13]2[S:14][C:15]([CH2:19][C:20]([O:22]CC)=[O:21])=[C:16]([CH3:18])[N:17]=2)=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5])C.CO.[OH-].[Na+]>O>[C:20]([CH2:19][C:15]1[S:14][C:13]([S:12][C:7]2[C:6]([C:4]([OH:5])=[O:3])=[CH:11][CH:10]=[CH:9][N:8]=2)=[N:17][C:16]=1[CH3:18])([OH:22])=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 737 mg (2.09 mmol) of the title compound of Example 1, 70 ml of methanol, and 30 ml of water chilled to 0° C. in an ice bath was added 210 mg (5.22 mmol, 2.5 equivalents) of sodium hydroxide. After the sodium hydroxide had dissolved, the ice bath was removed and the mixture was allowed to stir at room temperature for 3 hours. The solvent was removed by rotary evaporation and the residue was diluted with water, chilled to 0° C. in an ice bath, and acidified with aqueous 6N HCl solution until precipitation had ceased. The precipitate was collected by filtration (washed with cold water) and was dried under vacuum to yield 554 mg (85%) of the title compound, mp 233°-235° C. 1H NMR (DMSO-d6): δ 2.29 (3H, s), 3.85 (2H, s), 7.38 (1H, dd, J=8, 5), 8.33 (1H, d, J=8), 8.63 (1H, d, J=5). FAB MS (m/e): 311 (M+ +1), 265, 233, 119 (base).

Workup

customthe ice bath was removed
customThe solvent was removed by rotary evaporation
additionthe residue was diluted with water
temperaturechilled to 0° C. in an ice bath
customacidified with aqueous 6N HCl solution until precipitation
filtrationThe precipitate was collected by filtration (washed with cold water)
customwas dried under vacuum

Sources & evidence

ORD record: ord-dec2a973edfc46f5a65f9a6678c1da45
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05789408

Reaction notes

Loading…