(2-Amino-1,3-thiazol-4-yl)acetic acid → HCID 86757437, compound

HRID 1597693Notes

Reaction equation

HRID 1597693 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:13][C:14]1[S:15][CH:16]=[C:17]([CH2:19][C:20]([OH:22])=O)[N:18]=1.FC(F)(F)C([O-])=O.[NH2:30][C@@H:31]1[C:38](=[O:39])[N:37]2[C@@H:32]1[S:33][CH2:34][C:35](/[CH:43]=[C:44]1/[C:45](=[O:67])[N:46]([CH2:49][C:50]3[CH:55]=[CH:54][N+:53]([CH2:56][C:57](=[O:66])[NH:58][C:59]4[CH:64]=[CH:63][C:62]([OH:65])=[CH:61][CH:60]=4)=[CH:52][CH:51]=3)[CH2:47][CH2:48]/1)=[C:36]2[C:40]([OH:42])=[O:41]>CN(C)C=O>[NH2:13][C:14]1[S:15][CH:16]=[C:17]([CH2:19][C:20]([NH:30][C@@H:31]2[C:38](=[O:39])[N:37]3[C@@H:32]2[S:33][CH2:34][C:35](/[CH:43]=[C:44]2/[C:45](=[O:67])[N:46]([CH2:49][C:50]4[CH:51]=[CH:52][N+:53]([CH2:56][C:57](=[O:66])[NH:58][C:59]5[CH:60]=[CH:61][C:62]([OH:65])=[CH:63][CH:64]=5)=[CH:54][CH:55]=4)[CH2:47][CH2:48]/2)=[C:36]3[C:40]([O-:42])=[O:41])=[O:22])[N:18]=1

Participants

5

Reactant 3

HCID 34665(2-Amino-1,3-thiazol-4-yl)acetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 86757436HCID 86757436, compound

Product 1

HCID 86757437HCID 86757437, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

With 54.5 mg (0.34 mmol) 1,1′-carbonyldiimidazole, 53.0 mg (0.34 mmol) (2-aminothiazole-4-yl)-acetic acid and 182.0 mg (0.28 mmol) (E)-(6R,7R)-7-amino-3-[1-[1-[(4-hydroxy-phenylcarbamoyl)-methyl]-pyridin-1-ium-4-ylmethyl]-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate trifluoroacetate in 4 ml N,N-dimethylformamide. The resulting solid was purified by reversed phase chromatography (RP-18 LiChroPrep gel, water:acetonitrile=9:1). The organic solvent was stripped off at a rotary evaporator and the aqueous phase was freeze-dried.

Workup

  1. customThe resulting solid was purified by reversed phase chromatography (RP-18 LiChroPrep gel, water:acetonitrile=9:1)
  2. customThe organic solvent was stripped off at a rotary evaporator
  3. customthe aqueous phase was freeze-dried

Sources & evidence

ORD record
ord-70905708d6be46b59999bbb4e36f0579
Source dataset
uspto-grants-2001_09
Patent number
US06294668B1

Reaction notes

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