Hydrochloric Acid → (4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyloxymethyl)-1-formimidoylpyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

HRID 703611Notes

Reaction equation

HRID 703611 reaction equation
[F:1][CH2:2][CH2:3][O:4][CH2:5][C@@H:6]1[CH2:10][C@H:9]([S:11][C:12]2[C@H:18]([CH3:19])[C@H:17]3[N:14]([C:15](=[O:23])[C@@H:16]3[C@H:20]([OH:22])[CH3:21])[C:13]=2[C:24]([OH:26])=[O:25])[CH2:8][NH:7]1.Cl.[CH:28](=[NH:37])OCC1C=CC=CC=1.[OH-].[Na+].Cl>O>[F:1][CH2:2][CH2:3][O:4][CH2:5][C@@H:6]1[CH2:10][C@H:9]([S:11][C:12]2[C@H:18]([CH3:19])[C@H:17]3[N:14]([C:15](=[O:23])[C@@H:16]3[C@H:20]([OH:22])[CH3:21])[C:13]=2[C:24]([OH:26])=[O:25])[CH2:8][N:7]1[CH:28]=[NH:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13116802Benzyl formimidate hydrochlorideHCID 86744488FR-27743

Product 1

HCID 86744495(4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyloxymethyl)-1-formimidoylpyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.3 g) in water (90 ml) was added benzyl formimidate hydrochloride (0.4 g) under ice-cooling with stirring, keeping the pH between 8.5-9 with 4N aqueous sodium hydroxide. After stirring for 30 minutes, the mixture was adjusted to pH 6.5 with 1N hydrochloric acid and washed with ethyl acetate (60 ml×3). The aqueous layer was subjected to a column chromatography on nonionic adsorption resin, "Diaion HP-20" (10 ml), washed with water, eluted with a mixture of acetone and water (7:93 V/V), and lyophilized to give (4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyloxymethyl)-1-formimidoylpyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid [0.2 g).

Workup

  1. temperaturecooling
  2. stirringAfter stirring for 30 minutes
  3. washwashed with ethyl acetate (60 ml×3)
  4. wash" (10 ml), washed with water
  5. washeluted with a mixture of acetone and water (7:93 V/V)

Sources & evidence

ORD record
ord-e9921031c5d84003a3a7ad90c48e921a
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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