Hydrochloric Acid → (S)-[1-[[[[3-[[(1,4-Dihydro-5-hydroxy-4-oxo-2-pyridinyl)carbonyl]amino]tetrahydro-2-oxo-1(2H)-pyrimidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

HRID 2351086Notes

Reaction equation

HRID 2351086 reaction equation
[OH:1][C:2]1[C:3](=[O:18])[CH:4]=[C:5]([C:8]([NH:10][N:11]2[CH2:16][CH2:15][CH2:14][NH:13][C:12]2=[O:17])=[O:9])[NH:6][CH:7]=1.CN([Si](C)(C)C)C(=O)C(F)(F)F.N1CCCNC1=O.[O:38]=[C:39]1[C@@H:42]([NH:43][C:44](=[O:53])[O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:41][NH:40]1.Cl[S:55]([N:58]=[C:59]=[O:60])(=[O:57])=[O:56].Cl>C(OCC)(=O)C.ClCCl>[OH:1][C:2]1[C:3](=[O:18])[CH:4]=[C:5]([C:8]([NH:10][N:11]2[CH2:16][CH2:15][CH2:14][N:13]([S:55]([NH:58][C:59]([N:40]3[CH2:41][C@H:42]([NH:43][C:44](=[O:53])[O:45][CH2:46][C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)[C:39]3=[O:38])=[O:60])(=[O:57])=[O:56])[C:12]2=[O:17])=[O:9])[NH:6][CH:7]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 70918Chlorosulfonyl isocyanateHCID 746152(1H)-Pyrimidinone, tetrahydro-2×HCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamateHCID 198480131,4-Dihydro-5-hydroxy-4-oxo-N-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)-2-pyridinecarboxamide

Product 1

HCID 86743424(S)-[1-[[[[3-[[(1,4-Dihydro-5-hydroxy-4-oxo-2-pyridinyl)carbonyl]amino]tetrahydro-2-oxo-1(2H)-pyrimidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

2.73 g (10.82 mmol) 1,4-dihydro-5-hydroxy-4-oxo-N-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)-2-pyridinecarboxamide and 8.63 g (43.29 mmol) N-methyl-N-trimethylsilyltrifluoroacetamide were dissolved in ethyl acetate and stirred for 1 hour (solution A). To a suspension of 2.38 g (10.82 mmol) (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 80 ml ethyl acetate was added 1.53 g (10.82 mmol) chlorosulfonyl isocyanate. After stirring for 1 hour, the solution was cooled to 0° C. and 9 ml dichloromethane and subsequently solution A were added. After stirring overnight at room temperature ice water was added and the pH was adjusted to 1.3 with 3N hydrochloric acid. The precipitate was filtered off, washed with water, dried in vacuo and slurried with ether. Yield 4.95 g, melting range 150°-230° C. (dec.).

Workup

  1. additionwas added
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d6b1ec5eeed344889ebecb40d77e4209
Source dataset
uspto-grants-1989_10
Patent number
US04871841

Reaction notes

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