N-methyl-N-(trimethylsilyl)trifluoroacetamide → 2-[[[1-(2-Amino-4-thiazolyl)-2-[[1-[[[[3-[[(1,4-dihydro-6,7-dihydroxy-4-oxo-3-quinolinyl)carbonyl]amino]-2-oxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid, diphenylmethyl ester

HRID 868149Notes

Reaction equation

HRID 868149 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[NH:8][CH:7]=[C:6]([C:13]([NH:15][N:16]1[CH2:20][CH2:19][N:18]([S:21]([NH:24][C:25]([N:27]3[CH2:30][CH:29]([NH:31][C:32](=[O:41])OCC4C=CC=CC=4)[C:28]3=[O:42])=[O:26])(=[O:23])=[O:22])[C:17]1=[O:43])=[O:14])[CH2:5]2.CN([Si](C)(C)C)C(=[O:51])C(F)(F)F.[NH2:56][C:57]1[S:58][CH:59]=[C:60](/[C:62](=[N:66]/[O:67][C:68]([CH3:86])([CH3:85])[C:69]([O:71][CH:72]([C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)[C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)=[O:70])/C(O)=O)[N:61]=1>CN(C)C=O.[Pd]>[NH2:56][C:57]1[S:58][CH:59]=[C:60]([C:62](=[N:66][O:67][C:68]([CH3:86])([CH3:85])[C:69]([O:71][CH:72]([C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)[C:73]2[CH:74]=[CH:75][CH:76]=[CH:77][CH:78]=2)=[O:70])[C:32]([NH:31][CH:29]2[CH2:30][N:27]([C:25]([NH:24][S:21]([N:18]3[CH2:19][CH2:20][N:16]([NH:15][C:13]([C:6]4[C:5](=[O:51])[C:4]5[C:9](=[CH:10][C:11]([OH:12])=[C:2]([OH:1])[CH:3]=5)[NH:8][CH:7]=4)=[O:14])[C:17]3=[O:43])(=[O:23])=[O:22])=[O:26])[C:28]2=[O:42])=[O:41])[N:61]=1

Participants

6

Reactant 3

HCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 135359672-Amino-alpha-((2-(diphenylmethoxy)-1,1-dimethyl-2-oxoethoxy)imino)thiazol-4-acetic acidHCID 86742476[1-[[[[3-[[(1,4-Dihydro-6,7-dihydroxy-3-quinolinyl)carbonyl]amino]-2-oxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

Product 1

HCID 867424752-[[[1-(2-Amino-4-thiazolyl)-2-[[1-[[[[3-[[(1,4-dihydro-6,7-dihydroxy-4-oxo-3-quinolinyl)carbonyl]amino]-2-oxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid, diphenylmethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of [1-[[[[3-[[(1,4-dihydro-6,7-dihydroxy-3-quinolinyl)carbonyl]amino]-2-oxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester (3.35 g, 5.3 mmol) in 60 ml of N,N-dimethylformamide, N-methyl-N-trimethylsilyl trifluoroacetamide (5.28 g, 26.5 mmol) was added. After 30 minutes, 1.68 g of palladium on carbon was added, and the mixture was hydrogenolyzed for 1 hour. The catalyst was removed by filtration and the filtrate added to a solution of (Z)-2-amino-α-[[2-(diphenylmethoxy)-1,1-dimethyl-2-oxoethoxy]imino]-4-thiazoleacetic acid, 1-benzotriazole ester (2.96 g, 5.3 mmol) in 30 ml of N,N-dimethylformamide. After stirring for 20 hours, the solvent was distilled off and the residue triturated with 60 ml of water and 75 ml of ethyl acetate. The resulting crystals were filtered off, washed with water and dried in vacuo to give 3.27 g of the title compound.

Workup

  1. waitthe mixture was hydrogenolyzed for 1 hour
  2. customThe catalyst was removed by filtration
  3. distillationthe solvent was distilled off
  4. customthe residue triturated with 60 ml of water and 75 ml of ethyl acetate
  5. filtrationThe resulting crystals were filtered off
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-a63c0aea668a424c99324d7eb3442978
Source dataset
uspto-grants-1988_10
Patent number
US04777252

Reaction notes

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