Sodium Carbonate → HCID 178462292, compound

HRID 1840447Notes

Reaction equation

HRID 1840447 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][C:5]1[N:6]=[CH:7][N:8]2[CH:12]=[C:11]([C:13]3[C@H:14]([CH3:27])[C@@H:15]4[C@@H:22]([C@H:23]([OH:25])[CH3:24])[C:21](=[O:26])[N:16]4[C:17]=3[C:18]([O-:20])=[O:19])[S:10][C:9]=12.[Na+:28].Cl.C(O[CH:33]=[NH:34])C.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH:33]([NH:1][CH2:2][CH2:3][S:4][C:5]1[N:6]=[CH:7][N:8]2[CH:12]=[C:11]([C:13]3[C@H:14]([CH3:27])[C@@H:15]4[C@@H:22]([C@H:23]([OH:25])[CH3:24])[C:21](=[O:26])[N:16]4[C:17]=3[C:18]([O-:20])=[O:19])[S:10][C:9]=12)=[NH:34].[Na+:28]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 12578842Ethyl formimidate hydrochlorideHCID 131724313HCID 131724313, compound

Product 1

HCID 178462292HCID 178462292, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium (1S,5R,6S)-2-[7-(2-aminoethyl)thioimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate (45.7 mg) was suspended in 3 ml of water under ice cooling. Ethylformimidate hydrochloride (46 mg) was added to the suspension. While adjusting the mixture to pH 8 to 9 by the addition of an aqueous sodium carbonate solution, the mixture was stirred at that temperature for one hr, and then at room temperature for 1.5 hr. The reaction product was then purified by column chromatography on Cosmosil 40C18-PREP (a 20% aqueous methanol solution) to prepare 5.4 mg of the title compound.

Workup

  1. waitat room temperature for 1.5 hr
  2. customThe reaction product was then purified by column chromatography on Cosmosil 40C18-PREP (a 20% aqueous methanol solution)
  3. customto prepare 5.4 mg of the title compound

Sources & evidence

ORD record
ord-cf8d1d39328041da843d8ec8899b854e
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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