Pyridine → 6-(2-Phenylacetamido)-2,2-dimethyl-3-phosphonopenam

HRID 1833431Notes

Reaction equation

[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:24](=[O:25])[N:13]3[CH:14]([P:19]([OH:23])([O:21]C)=[O:20])[C:15]([CH3:18])([CH3:17])[S:16][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.C[Si](C)(C)Cl.[I-].[Li+]>O>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:24](=[O:25])[N:13]3[CH:14]([P:19]([OH:23])([OH:21])=[O:20])[C:15]([CH3:18])([CH3:17])[S:16][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 25 °C

Procedure

6-(2-phenylacetamido)-2,2-dimethyl-3-(O-methylphosphono)penam (384 mg., 1.0 millimole) is dissolved in 4 ml. of dry pyridine then trimethylchlorosilane (0.381 ml., 3.0 millimoles) and lithium iodide (536 mg., 4.0 millimoles) are added. The reaction mixture is stirred under nitrogen at 25° C. for 5 hours after which 2 ml. of water is added. The mixture is stirred for 10 minutes then the volatiles removed by evaporation in vacuo. The residue was taken up in water, adjusted to pH 8.0 and extracted with 3 × 10 ml. of chloroform. The aqueous phase was then acidified to pH 1.5 and extracted with 3 × 10 ml. of ethyl acetate. The ethyl acetate extracts were dried over sodium sulfate then evaporated to dryness to obtain the title compound.

Workup

stirringThe mixture is stirred for 10 minutes
customthe volatiles removed by evaporation in vacuo
extractionextracted with 3 × 10 ml
extractionextracted with 3 × 10 ml
dry with materialThe ethyl acetate extracts were dried over sodium sulfate
customthen evaporated to dryness

Sources & evidence

ORD record: ord-3cf3931f114641e0830c799e2a28a5ac
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04066657

Reaction notes

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