Trimethylamine → HCID 88701876, compound

HRID 1463153Notes

Reaction equation

HRID 1463153 reaction equation
O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:14][CH:15]1[C:30](=[O:31])[N:17]2[C:18]([C:27]([OH:29])=[O:28])=[C:19]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[CH2:20][S:21][C@H:16]12.C[Si](C)(C)Cl.C[C:38](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:39].CN(C)C>C1COCC1.O.C(N(CC)CC)C>[C:24]([O:23][CH2:22][C:19]1[CH2:20][S:21][C@@H:16]2[CH:15]([NH:14][CH:38]=[O:39])[C:30](=[O:31])[N:17]2[C:18]=1[C:27]([OH:29])=[O:28])(=[O:26])[CH3:25]

Participants

8

Reactant 4

HCID 1146TrimethylamineHCID 6397Chlorotrimethylsilane3×HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester2×HCID 131713624HCID 131713624, compound

Product 1

HCID 88701876HCID 88701876, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent2×

Procedure

To a stirred suspension of 7-amino-3-acetoxymethylceph-3-em-4-carboxylic acid toluene-p-sulphonate dihydrate (19.2 g., 40 mmole) in anhydrous THF (500 ml.) under nitrogen in a 1 liter flask was added triethylamine (dried over potassium, 27.76 ml., 200 mmole) then trimethylchlorosilane (20.18 ml., 17.36 g., 160 mmole) while maintaining the temperature at 20° with a cooling bath. After 30 minutes a further 10% of triethylamine and 10% of trimethylchlorosilane were added and the reaction mixture was allowed to stir for a further 2.5 hours. To the mixture was then added acetic formic mixed anhydride (7.04 g., 80 mmole) with cooling in an ice bath. A further 10% trimethylamine, 10% trimethylchlorosilane and 20% acetic formic mixed anhydride, and then yet a further 10% of all three reagents were added to achieve complete disappearance of starting material on t.l.c. Water was then added, the suspension was filtered on a sintered glass disc and the solid dried to give 3-acetoxymethyl-7-formylaminoceph-3-em-4-carboxylic acid.

Workup

  1. temperaturewith cooling in an ice bath
  2. filtrationthe suspension was filtered on a sintered glass disc
  3. customthe solid dried

Sources & evidence

ORD record
ord-30a3be3e1ebf46c0bf44882ff240d0ca
Source dataset
uspto-grants-1984_07
Patent number
US04463173

Reaction notes

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