Pyridine → HCID 69469743, compound

HRID 1799704Notes

Reaction equation

HRID 1799704 reaction equation
N1C=CC=CC=1.[C:7](OC(=O)C)(=[O:9])[CH3:8].[OH:14][CH2:15][C:16]1[N:17]=[CH:18][S:19][C:20]=1/[CH:21]=[CH:22]\[S:23][C:24]1[C@H:25]([CH3:55])[C@@H:26]2[C@@H:43]([C@H:44]([O:46][Si:47]([CH2:52][CH3:53])([CH2:50][CH3:51])[CH2:48][CH3:49])[CH3:45])[C:42](=[O:54])[N:27]2[C:28]=1[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1)=[O:30].C(OCC)(=O)C>C1COCC1>[C:7]([O:14][CH2:15][C:16]1[N:17]=[CH:18][S:19][C:20]=1/[CH:21]=[CH:22]\[S:23][C:24]1[C@H:25]([CH3:55])[C@@H:26]2[C@@H:43]([C@H:44]([O:46][Si:47]([CH2:50][CH3:51])([CH2:48][CH3:49])[CH2:52][CH3:53])[CH3:45])[C:42](=[O:54])[N:27]2[C:28]=1[C:29]([O:31][CH2:32][C:33]1[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=1)=[O:30])(=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 69469395HCID 69469395, compound

Product 1

HCID 69469743HCID 69469743, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N-Dimethylaminopyridine (37 mg), 0.133 ml of pyridine, and 0.114 ml of acetic anhydride were added to 3 ml of a solution of 695 mg of 4-nitrobenzyl (1R,5S,6S)-2-[[(Z)-2-(4-hydroxymethylthiazol-5-yl)ethen-1-yl]thio]-1-methyl-6-((1R)-1-triethylsilyloxyethyl)-1-carbapen-2-em-3-carboxylate in THF, and the mixture was stirred at room temperature for 1.5 hr. Ethyl acetate was added to the reaction solution, and the mixture was washed with brine, was dried over anhydrous magnesium sulfate, and was filtered. Silica gel (5 g) was added to the filtrate, the mixture was filtered, and the filtrate was concentrated under the reduced pressure to give 730 mg of 4-nitrobenzyl (1R,5S,6S)-2-[[(Z)-2-(4-acetoxymethylthiazol-5-yl)ethen-1-yl]thio]-1-methyl-6-((1R)-1-triethylsilyloxyethyl)-1-carbapen-2-em-3-carboxylate.

Workup

  1. washthe mixture was washed with brine
  2. dry with materialwas dried over anhydrous magnesium sulfate
  3. filtrationwas filtered
  4. additionSilica gel (5 g) was added to the filtrate
  5. filtrationthe mixture was filtered
  6. concentrationthe filtrate was concentrated under the reduced pressure

Sources & evidence

ORD record
ord-4d4c2141ed154a2d803ebff8095dbc15
Source dataset
uspto-grants-2013_01
Patent number
US08344154B2

Reaction notes

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