N-methyl-N-(trimethylsilyl)trifluoroacetamide → HCID 70463777, compound

HRID 1902915Notes

Reaction equation

HRID 1902915 reaction equation
CN([Si:9]([CH3:12])([CH3:11])[CH3:10])C(=O)C(F)(F)F.[CH3:13][C:14]1[CH2:15][S:16](=[O:36])[C@@H:17]2[CH:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:23](=[O:35])[N:18]2[C:19]=1[C:20]([OH:22])=[O:21].[Br:37]N1C(=O)CCC1=O>ClC1C=CC=CC=1Cl>[Br:37][CH2:13][C:14]1[CH2:15][S:16](=[O:36])[C@@H:17]2[CH:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:23](=[O:35])[N:18]2[C:19]=1[C:20]([O:22][Si:9]([CH3:12])([CH3:11])[CH3:10])=[O:21]

Participants

5

Reactant 3

HCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 67184N-bromobutanimideHCID 70485748HCID 70485748, compound

Product 1

HCID 70463777HCID 70463777, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent2×

Procedure

0.3 ml of N-methyl-N-trimethylsilyltrifluoroacetamide (1.6 mmoles) was added at room temperature to a suspension of 354 mg (1.02 mmoles) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide in 40 ml of o-dichlorobenzene and after stirring for 15 minutes, 20 ml of o-dichlorobenzene were added thereto. Bromination was carried out as described in Example 37 using 310 mg (1.74 mmoles) of N-bromosuccinimide as the brominating agent and irradiation was continued for 80 minutes to obtain trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide in a yield of 45%.

Workup

  1. waitwas continued for 80 minutes

Sources & evidence

ORD record
ord-17b8183c90024caca3a38b5809febe1d
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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