Bromotrimethylsilane → (6R,7R)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(phosphonocarbamoyloxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 894825Notes

Reaction equation

HRID 894825 reaction equation
Br[Si](C)(C)C.C[O:7][P:8]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH2:18][S:19][C@@H:20]2[C@H:27]([NH:28][C:29](=[O:39])/[C:30](/[C:34]3[O:35][CH:36]=[CH:37][CH:38]=3)=[N:31]\[O:32][CH3:33])[C:26](=[O:40])[N:21]2[C:22]=1[C:23]([OH:25])=[O:24])=[O:14])([O:10]C)=[O:9].C[Si](NC(OCC)=O)(C)C>ClCCl>[P:8]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH2:18][S:19][C@@H:20]2[C@H:27]([NH:28][C:29](=[O:39])/[C:30](/[C:34]3[O:35][CH:36]=[CH:37][CH:38]=3)=[N:31]\[O:32][CH3:33])[C:26](=[O:40])[N:21]2[C:22]=1[C:23]([OH:25])=[O:24])=[O:14])([OH:9])([OH:10])=[O:7]

Participants

5

Reactant 3

HCID 76113BromotrimethylsilaneHCID 11355656N-trimethylsilylurethaneHCID 88764320(6R,7R)-3-(dimethoxyphosphorylcarbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 88760882(6R,7R)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(phosphonocarbamoyloxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Bromotrimethylsilane (0.61 g), in dichloromethane (3 ml) was added (at 0° under nitrogen) to a stirred solution of (6R,7R)-3-dimethoxyphosphorylcarbamoyloxymethyl-7-[Z-2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylic acid (0.53 g) and trimethylsilylurethane (0.965 g) in dry dichloromethane (5 ml). After 1.75 hours no starting cephalosporin remained as indicated by t.l.c.

Sources & evidence

ORD record
ord-1ba7a33139484ec0a62fe7bfe6eca9cc
Source dataset
uspto-grants-1981_08
Patent number
US04284766

Reaction notes

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