Methanesulfonic Acid → HCID 13319610, compound

HRID 2413432Notes

Reaction equation

CS(O)(=O)=O.[CH:6]([O:19][C:20]([C:22]1[N:23]2[CH:26]([S:27][CH2:28][C:29]=1[C:30]1[S:34][C:33]([NH:35][CH2:36][CH2:37][N:38]([CH3:40])[CH3:39])=[N:32][CH:31]=1)[CH:25]([NH:41]C(OC(C)(C)C)=O)[C:24]2=[O:49])=[O:21])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(#N)C>[NH2:41][CH:25]1[C:24](=[O:49])[N:23]2[CH:26]1[S:27][CH2:28][C:29]([C:30]1[S:34][C:33]([NH:35][CH2:36][CH2:37][N:38]([CH3:40])[CH3:39])=[N:32][CH:31]=1)=[C:22]2[C:20]([O:19][CH:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:21]

Participants

Conditions

Temperature: 23 °C

Procedure

Methanesulphonic acid (0.3 cc) is added to a suspension of 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-[2-(2-dimethylamino-ethylamino)-thiazol-5-yl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (0.3 g) in acetonitrile (3 cc). The yellow solution obtained is stirred at 23° C. for 5 minutes and is poured onto a mixture of a saturated sodium bicarbonate solution (50 cc) and ethyl acetate (50 cc). The organic phase is dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure (20 mm Hg; 2.7 kPa). 7-Amino-2-benzhydryloxycarbonyl-3-[2-(2-dimethylamino-ethylamino)-thiazol-5-yl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (0.25 g) is thus obtained in the form of a yellow froth.

Workup

customThe yellow solution obtained
dry with materialThe organic phase is dried over anhydrous magnesium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure (20 mm Hg; 2.7 kPa)

Sources & evidence

ORD record: ord-d4711ea2fd134abdb04d4e3591272c69
Source dataset: uspto-grants-1985_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04496560

Reaction notes

Loading…