(2-Amino-1,3-thiazol-4-yl)acetic acid → HCID 86757439, compound

HRID 1597694Notes

Reaction equation

HRID 1597694 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.[NH2:23][C@@H:24]1[C:31](=[O:32])[N:30]2[C@@H:25]1[S:26][CH2:27][C:28](/[CH:36]=[C:37]1/[C:38](=[O:46])[N:39]([CH2:42][CH:43]3[CH2:45][CH2:44]3)[CH2:40][CH2:41]/1)=[C:29]2[C:33]([OH:35])=[O:34]>CN(C)C=O>[NH2:13][C:14]1[S:15][CH:16]=[C:17]([CH2:19][C:20]([NH:23][C@@H:24]2[C:31](=[O:32])[N:30]3[C@@H:25]2[S:26][CH2:27][C:28](/[CH:36]=[C:37]2/[C:38](=[O:46])[N:39]([CH2:42][CH:43]4[CH2:45][CH2:44]4)[CH2:40][CH2:41]/2)=[C:29]3[C:33]([OH:35])=[O:34])=[O:22])[N:18]=1

Participants

5

Reactant 3

HCID 34665(2-Amino-1,3-thiazol-4-yl)acetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 10689147(E)-(6R,7R)-7-Amino-3-(1-cyclopropylmethyl-2-oxo-pyrrolidin-3-ylidenemethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 86757439HCID 86757439, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

With 167.0 mg (1.03 mmol) 1,1′-carbonyldiimidazole, 163.0 mg (1.03 mmol) (2-aminothiazole-4-yl)-acetic acid and 300.0 mg (0.86 mmol) (E)-(6R,7R)-7-amino-3-(1-cyclopropylmethyl-2-oxo-pyrrolidin-3-ylidenemethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid in 6 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-1fc7456cb51646e28b2e97baff1b0903
Source dataset
uspto-grants-2001_09
Patent number
US06294668B1

Reaction notes

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