Triethylamine → (3S)-3-[[(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-N-[(5-methyl-1,2-thiazol-3-yl)sulfamoyl]-2-oxoazetidine-1-carboxamide

HRID 1166005Notes

Reaction equation

HRID 1166005 reaction equation
C(N(CC)CC)C.FC(F)(F)C(O)=O.[NH2:15][C@H:16]1[CH2:19][N:18]([C:20]([NH:22][S:23]([NH:26][C:27]2[CH:31]=[C:30]([CH3:32])[S:29][N:28]=2)(=[O:25])=[O:24])=[O:21])[C:17]1=[O:33].Cl.[Cl:35][CH2:36][C:37]([NH:39][C:40]1[S:41][CH:42]=[C:43](/[C:45](=[N:49]/[O:50][CH3:51])/[C:46](Cl)=[O:47])[N:44]=1)=[O:38]>CN(C=O)C.C(Cl)(Cl)Cl>[Cl:35][CH2:36][C:37]([NH:39][C:40]1[S:41][CH:42]=[C:43](/[C:45](=[N:49]/[O:50][CH3:51])/[C:46]([NH:15][C@H:16]2[CH2:19][N:18]([C:20]([NH:22][S:23]([NH:26][C:27]3[CH:31]=[C:30]([CH3:32])[S:29][N:28]=3)(=[O:24])=[O:25])=[O:21])[C:17]2=[O:33])=[O:47])[N:44]=1)=[O:38]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12884125(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl chloride;hydrochlorideHCID 70361265(S)-3-amino-N-[[(5-methyl-3-isothiazolyl)amino]sulfonyl]-2-oxo-1-azetidinecarboxamide trifluoroacetic acid salt

Product 1

HCID 88607109(3S)-3-[[(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-N-[(5-methyl-1,2-thiazol-3-yl)sulfamoyl]-2-oxoazetidine-1-carboxamideYield 61.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 436 mg (4.32 mmol) of triethylamine in 3.2 mL of dry DMF was cooled to -8° C. and 502 mg (1.2 mmol) of (S)-3-amino-N-[[(5-methyl-3-isothiazolyl)amino]sulfonyl]-2-oxo-1-azetidinecarboxamide trifluoroacetic acid salt was added. To the resulting solution was added dropwise a solution of 520 mg (1.2 mmol) of (Z)-[2-(chloroacetyl)amino-4-thiazolyl](methoxyimino)acetyl chloride hydrochloride in 4 mL of chloroform. The mixture was stirred cold for 15 minutes and at room temperature for three hours before concentrating under reduced pressure. Methylene chloride was added to the residue, and evaporation under reduced pressure was repeated. The residue was taken up in ethyl acetate and water, and the mixture adjusted to pH3 with N hydrochloric acid. The organic phase was washed with brine, dried (Na2SO4), decolorized with charcoal, and concentrated under reduced pressure to obtain 420 mg of the title compound.

Workup

  1. concentrationbefore concentrating under reduced pressure
  2. additionMethylene chloride was added to the residue, and evaporation under reduced pressure
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c8d688bbd5314ad2beb2eb95f3754534
Source dataset
uspto-grants-1990_03
Patent number
US04912214

Reaction notes

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