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

HRID 1029689
Notes
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Reaction equation

HRID 1029689 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[CH2:6][C:7]([CH:15]1[CH2:19][CH2:18][NH:17][CH2:16]1)=[C:8]2[C:12]([OH:14])=[O:13])[CH3:3].Cl.[CH:21](=[NH:30])OCC1C=CC=CC=1.[OH-].[Na+].Cl>>[CH:21]([N:17]1[CH2:18][CH2:19][CH:15]([C:7]2[CH2:6][C@H:5]3[N:9]([C:10](=[O:11])[C@@H:4]3[C@H:2]([OH:1])[CH3:3])[C:8]=2[C:12]([OH:14])=[O:13])[CH2:16]1)=[NH:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13116802Benzyl formimidate hydrochlorideHCID 15117376(5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-(pyrrolidin-3-yl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Product 1

HCID 15117383(5R,6S)-3-(1-formimidoylpyrrolidin-3-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Yield 43.6%

Procedure

To a solution of (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-(pyrrolidin-3-yl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (250 mg) was added benzyl formimidate hydrochloride (0.48 g) at 0° C. while adjusting pH to 8.5 with 30% aqueous sodium hydroxide solution. After 30 minutes at the same temperature, the solution was adjusted to pH 6.5 with 1N hydrochloric acid, washed with ethyl acetate and concentrated in vacuo. The residue was chromatographed on nonionic adsorption resin "Diaion HP-20" (Trademark, made by Mitsubishi Chemical Industries) eluting with 3% aqueous isopropyl alcohol. The fractions containing the desired compound were collected and lyophilized to give (5R,6S)-3-(1-formimidoylpyrrolidin-3-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (120 mg).

Workup

  1. washwashed with ethyl acetate
  2. concentrationconcentrated in vacuo
  3. customThe residue was chromatographed on nonionic adsorption resin "Diaion
  4. wash" (Trademark, made by Mitsubishi Chemical Industries) eluting with 3% aqueous isopropyl alcohol
  5. additionThe fractions containing the desired compound
  6. customwere collected

Sources & evidence

ORD record
ord-2c2bccfc18444db28ad06482d2c19460
Source dataset
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05102877

Reaction notes

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