Hydrochloric Acid → HCID 3309686, compound

HRID 975184Notes

Reaction equation

[CH3:1][C:2]([O:4][CH2:5][C:6]1[CH2:25][S:24][C@@H:9]2[C@H:10]([NH:13][C:14]([C@H:16]([NH2:23])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:15])[C:11](=[O:12])[N:8]2[C:7]=1[C:26]([OH:28])=[O:27])=[O:3].Cl>>[C:2]([O:4][CH2:5][C:6]1[CH2:25][S:24][CH:9]2[N:8]([C:11](=[O:12])[CH:10]2[NH:13][C:14](=[O:15])[CH:16]([NH2:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7]=1[C:26]([OH:28])=[O:27])(=[O:3])[CH3:1]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 19150Cephaloglycin

Product 1

HCID 3309686HCID 3309686, compoundYield 84.2%

Conditions

Temperature: 25 °C

Procedure

The resultant crude protected cephaloglycin mixture is worked up by treating with a mixture of 27 ml ice-water and 6 ml concentrated HCl and stirred for 15 minutes while cooling with ice. The aqueous phase is separted off and the organic phase is back-extracted with 2 ml ice-water. The combined aqueous phases are heated to 25° C. and TEA is added until a pH value of 4.5/4.7 is reached. The title compound is obtained in the dihydrate form by standing the mixture 30 minutes, filtering the crystals and washing then with 30 ml ice-water and 30 ml 80% acetone, followed by drying. Yield 84.2%.

Workup

temperaturewhile cooling with ice
extractionthe organic phase is back-extracted with 2 ml ice-water
additionTEA is added until a pH value of 4.5/4.7

Sources & evidence

ORD record: ord-1298fe93693e4b5c89d9ff554c481daf
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05608055

Reaction notes

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