N-methyl-N-(trimethylsilyl)trifluoroacetamide → HCID 86742169, compound

HRID 1252630Notes

Reaction equation

HRID 1252630 reaction equation
[O:1]=[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][NH:5][C:4]([CH:16]=[CH:17][C:18]([NH:20][N:21]2[CH2:25][CH2:24][NH:23][C:22]2=[O:26])=[O:19])=[CH:3]1.CN([Si](C)(C)C)C(=O)C(F)(F)F.Cl[S:40]([NH:43][C:44]([N:46]1[CH2:49][C@H:48]([NH:50][C:51]([O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[O:52])[C:47]1=[O:61])=[O:45])(=[O:42])=[O:41]>C(OCC)(=O)C>[O:1]=[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][NH:5][C:4]([CH:16]=[CH:17][C:18]([NH:20][N:21]2[CH2:25][CH2:24][N:23]([S:40]([NH:43][C:44]([N:46]3[CH2:49][C@H:48]([NH:50][C:51](=[O:52])[O:53][CH2:54][C:55]4[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=4)[C:47]3=[O:61])=[O:45])(=[O:41])=[O:42])[C:22]2=[O:26])=[O:19])=[CH:3]1

Participants

5

Reactant 3

HCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 14326680HCID 14326680, compoundHCID 53698851HCID 53698851, compound

Product 1

HCID 86742169HCID 86742169, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

3-[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinyl]-N-(2-oxo-1-imidazolidinyl)-2-propenamide (3.55 g) was suspended in 100 ml of ethyl acetate and 6.3 g of N-methyl-N-(trimethylsilyl)trifluoroacetamide was added. After stirring for 1 hour, a clear solution was obtained. The solution was then added within 10 minutes to a cooled solution (0° C.) of 3.3 g of (S)-1-[[(chlorosulfonyl)amino]carbonyl]-3-[[(phenylmethoxy)carbonyl]amino]-2-azetidinone in 50 ml of ethyl acetate. After stirring overnight, the solvent was evaporated and the oily residue was stirred for 1 hour with 50 ml of isopropanol. The resultant precipitate was isolated by filtration and washed with isopropanol and ether. Yield: 5.91 g.

Workup

  1. customa clear solution was obtained
  2. stirringAfter stirring overnight
  3. customthe solvent was evaporated
  4. stirringthe oily residue was stirred for 1 hour with 50 ml of isopropanol

Sources & evidence

ORD record
ord-096c24d02d8649c1aaf0e293609e4cbd
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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