Sodium Bicarbonate → HCID 23388249, compound

HRID 989879Notes

Reaction equation

HRID 989879 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.[Si]([O:31][CH2:32][C:33]1[N:34]=[C:35]([CH3:66])[N:36]2[CH:40]=[C:39]([C:41]3[C@H:42]([CH3:65])[C@@H:43]4[C@@H:60]([C@H:61]([OH:63])[CH3:62])[C:59](=[O:64])[N:44]4[C:45]=3[C:46]([O:48][CH2:49][C:50]3[CH:55]=[CH:54][C:53]([N+:56]([O-:58])=[O:57])=[CH:52][CH:51]=3)=[O:47])[S:38][C:37]=12)(C(C)(C)C)(C)C.C(=O)([O-])O.[Na+]>C(O)(=O)C>[OH:63][C@@H:61]([C@H:60]1[C:59](=[O:64])[N:44]2[C:45]([C:46]([O:48][CH2:49][C:50]3[CH:55]=[CH:54][C:53]([N+:56]([O-:58])=[O:57])=[CH:52][CH:51]=3)=[O:47])=[C:41]([C:39]3[S:38][C:37]4=[C:33]([CH2:32][OH:31])[N:34]=[C:35]([CH3:66])[N:36]4[CH:40]=3)[C@H:42]([CH3:65])[C@H:43]12)[CH3:62]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11078149TBAF tetrahydrofuranHCID 23388220HCID 23388220, compound

Product 1

HCID 23388249HCID 23388249, compoundYield 109%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Acetic acid (0.28 ml) and 1.6 ml of a 1 M tetrabutylammonium fluoride/THF solution were added to 313 mg of 4-nitrobenzyl(1S,5R,6S)-2-[7-(t-butyldimethylsilyloxy)methyl-5-methylimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate. The mixture was stirred at room temperature for 3.5 hr. The reaction solution was adjusted to pH 7 by the addition of a saturated aqueous sodium hydrogencarbonate solution. The reaction solution was then extracted with ethyl acetate, washed with saturated brine, and dried over magnesium sulfate. The reaction solution was then concentrated under the reduced pressure. The residue was purified by column chromatography to give 279 mg of 4-nitrobenzyl(1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(7-hydroxymethyl-5-methylimidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate.

Workup

  1. extractionThe reaction solution was then extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe reaction solution was then concentrated under the reduced pressure
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3f498d4bbb0e402d99fbcf7914b89a23
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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