Acetic Acid → HCID 131725341, compound

HRID 891525Notes

Reaction equation

HRID 891525 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:49]([CH3:51])[CH3:50])[C:12]([C:14]1[N:15]=[C:16]([N:19]2[CH2:22][CH:21]([S:23][C:24]3[C@H:25]([CH3:48])[C@@H:26]4[C@@H:43]([C@H:44]([OH:46])[CH3:45])[C:42](=[O:47])[N:27]4[C:28]=3[C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=3)=[O:30])[CH2:20]2)[S:17][CH:18]=1)=[O:13])(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[OH:8][CH2:9][CH2:10][N:11]([CH:49]([CH3:51])[CH3:50])[C:12]([C:14]1[N:15]=[C:16]([N:19]2[CH2:20][CH:21]([S:23][C:24]3[C@H:25]([CH3:48])[C@@H:26]4[C@@H:43]([C@H:44]([OH:46])[CH3:45])[C:42](=[O:47])[N:27]4[C:28]=3[C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=3)=[O:30])[CH2:22]2)[S:17][CH:18]=1)=[O:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 131725342HCID 131725342, compound

Product 1

HCID 131725341HCID 131725341, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

p-Nitrobenzyl (1R,5S,6S)-2-[1-(4-{N-[2-(t-butyldimethylsilyloxy)ethyl]-N-isopropyl-carbamoyl}-1,3-thiazol-2-yl)azetidin-3-yl]thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate (4.47 g, 5.88 mmol) (obtained as described in Example 64(1)) in a mixture of tetrahydrofuran (220 ml) was added to acetic acid (0.40 ml, 7.06 mmol) and 1M tetrabutylammonium fluoride in tetrahydrofuran solution (7.06 ml, 7.06 mmol) and the mixture was stirred at room temperature for 1 day. After checking the completion of the reaction, ethyl acetate and saturated aqueous sodium hydrogencarbonate solution were added to the reaction mixture. The resulting mixture was shaken in a separatory funnel and the ethyl acetate layer was separated, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluant: ethyl acetate→ethyl acetate:methanol (10:1)) to afford p-nitrobenzyl (1R,5S,6S)-2-(1-{4-[(2-hydroxyethyl)-isopropyl-carbamoyl]-1,3-thiazol-2-yl}azetidin-3-yl)thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate (1.79 g, yield 47%) as a pale yellow solid.

Workup

  1. additionwere added to the reaction mixture
  2. stirringThe resulting mixture was shaken in a separatory funnel
  3. customthe ethyl acetate layer was separated
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column (eluant: ethyl acetate→ethyl acetate:methanol (10:1))

Sources & evidence

ORD record
ord-5b2f6f526df348ddbf86de10dd84de5a
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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