N-methyl-N-(trimethylsilyl)trifluoroacetamide → HCID 178460183, compound

HRID 868163Notes

Reaction equation

HRID 868163 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[C:9]([O:20]CC3C=CC=CC=3)[C:10]([O:12]CC3C=CC=CC=3)=[CH:11][C:6]2=[N:5][CH:4]=[C:3]1[C:28]([NH:30][N:31]1[CH2:35][CH2:34][N:33]([S:36]([NH:39][C:40]([N:42]2[CH2:45][CH:44]([NH:46]C(=O)OCC3C=CC=CC=3)[C:43]2=[O:57])=[O:41])(=[O:38])=[O:37])[C:32]1=[O:58])=[O:29].CN([Si](C)(C)C)C(=O)C(F)(F)F.[NH2:71][C:72]1[S:73][CH:74]=[C:75](/[C:77](=[N:81]/[O:82][C:83]([CH3:101])([CH3:100])[C:84]([O:86][CH:87]([C:94]2[CH:99]=[CH:98][CH:97]=[CH:96][CH:95]=2)[C:88]2[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=2)=[O:85])/[C:78]([OH:80])=O)[N:76]=1>CN(C)C=O.[Pd]>[NH2:71][C:72]1[S:73][CH:74]=[C:75]([C:77](=[N:81][O:82][C:83]([CH3:101])([CH3:100])[C:84]([O:86][CH:87]([C:88]2[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=2)[C:94]2[CH:99]=[CH:98][CH:97]=[CH:96][CH:95]=2)=[O:85])[C:78]([NH:46][CH:44]2[CH2:45][N:42]([C:40]([NH:39][S:36]([N:33]3[CH2:34][CH2:35][N:31]([NH:30][C:28]([C:3]4[C:2](=[O:1])[N:7]5[CH:8]=[C:9]([OH:20])[C:10]([OH:12])=[CH:11][C:6]5=[N:5][CH:4]=4)=[O:29])[C:32]3=[O:58])(=[O:37])=[O:38])=[O:41])[C:43]2=[O:57])=[O:80])[N:76]=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 86742478[1-[[[[3-[[[4-oxo-7,8-bis(phenylmethoxy)-4H-pyrido[1,2-a]pyrimidin-3-yl]carbonyl]amino]-2-oxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

Product 1

HCID 178460183HCID 178460183, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of [1-[[[[3-[[[4-oxo-7,8-bis(phenylmethoxy)-4H-pyrido[1,2-a]pyrimidin-3-yl]carbonyl]amino]-2-oxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester (1.35 g, 1.66 mmol) in 65 ml of N,N-dimethylformamide, N-methyl-N-trimethylsilyl trifluoroacetamide (1.66 g, 8.33 mmol) was added. After 20 minutes 0.45 g of palladium on carbon was added, and the mixture was hydrogenolyzed for 1 hour. The catalyst was removed by filtration, and to the filtrate (Z)-2-amino-α-[[2-(diphenylmethoxy)-1,1-dimethyl-2-oxoethoxy]imino]-4-thiazoleacetic acid, 1-benzotriazole ester (0.83 g, 1.5 mmol) was added. After stirring overnight, the solvent was distilled off, and the residue triturated with 20 ml of water. The resulting solid was filtered off with suction and dried in vacuo. Yield of crude product: 1.28 g.

Workup

  1. customThe catalyst was removed by filtration
  2. distillationthe solvent was distilled off
  3. customthe residue triturated with 20 ml of water
  4. filtrationThe resulting solid was filtered off with suction
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ce328851eb3347bfbffa3b8a12635b7f
Source dataset
uspto-grants-1988_10
Patent number
US04777252

Reaction notes

Loading…