Chlorotrimethylsilane → Cephacetrile

HRID 2082664Notes

Reaction equation

HRID 2082664 reaction equation
[CH3:1][C:2]([O:4][CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=[O:3].C(N(CC)P1OCCO1)C.C[Si](C)(C)Cl.[C:34]([CH2:36][C:37](Cl)=[O:38])#[N:35]>C(Cl)Cl>[CH3:1][C:2]([O:4][CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH:13][C:37]([CH2:36][C:34]#[N:35])=[O:38])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=[O:3]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 1380361,3,2-Dioxaphospholane, 2-ethylamino-HCID 4413287-Aminocephalosporanic acidHCID 110515942-Cyanoacetyl chloride

Product 1

HCID 91562Cephacetrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.72 g (10 mmol) of 7-aminocephalosporanic acid are suspended in 50 ml of dry methylene chloride. 1.5 ml (10 mmol) of 2-diethylamino-1,3,2-dioxaphospholane and 1.33 ml (10.5 mmol) of trimethylchlorosilane are added under nitrogen at room temperature. The reaction mixture is stirred for 16 hours at room temperature. After cooling to 0° C, a solution of 10 mmol of cyanoacetyl chloride in 6 ml of methylene chloride is added over 5 minutes.

Workup

  1. temperatureAfter cooling to 0° C

Sources & evidence

ORD record
ord-d6b00c059bc94227a4358efce81baf31
Source dataset
uspto-grants-1978_04
Patent number
US04082745

Reaction notes

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