Sodium Bicarbonate → HCID 53643909, compound

HRID 1660396Notes

Reaction equation

[C:1]([O:4][CH:5]=[CH:6][C:7]1[CH2:14][S:13][CH:12]2[N:9]([C:10](=[O:23])[CH:11]2[NH:15]C(OC(C)(C)C)=O)[C:8]=1[C:24]([O:26][CH:27]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])(=[O:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(#N)C>[C:1]([O:4][CH:5]=[CH:6][C:7]1[CH2:14][S:13][CH:12]2[N:9]([C:10](=[O:23])[CH:11]2[NH2:15])[C:8]=1[C:24]([O:26][CH:27]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 3-(2-acetoxy-vinyl)-2-benzhydryloxycarbonyl-7-tert.-butoxycarbonylamino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (E-form) (1.65 g) (obtained as described above in Example 5), p-toluenesulphonic acid monohydrate (1.14 g) and acetonitrile (50 cc) is stirred for 16 hours at 20° C. It is then taken up in a 5% strength sodium bicarbonate solution (50 cc) and extracted with ethyl acetate (50 cc), and the organic phase is washed with a saturated sodium chloride solution (2×20 cc), dried over sodium sulphate and then concentrated to dryness under reduced pressure (20 mm Hg) at 20° C. 3-(2-Acetoxy-vinyl)-7-amino-2-benzhydryloxycarbonyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (E-form) (1.26 g) is obtained in the form of a crude red oil.

Workup

extractionextracted with ethyl acetate (50 cc)
washthe organic phase is washed with a saturated sodium chloride solution (2×20 cc)
dry with materialdried over sodium sulphate
concentrationconcentrated to dryness under reduced pressure (20 mm Hg) at 20° C

Sources & evidence

ORD record: ord-863a0f70618c493a81363365f012aaac
Source dataset: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04307230

Reaction notes

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