Hydrochloric Acid → HCID 18641567, compound

HRID 346380Notes

Reaction equation

HRID 346380 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[C@@H:6]([CH3:26])[C:7]([S:15][C@@H:16]1[CH2:20][NH:19][C@H:18]([CH2:21][O:22][CH2:23][CH2:24][OH:25])[CH2:17]1)=[C:8]2[C:12]([OH:14])=[O:13])[CH3:3].C(=O)([O-])[O-].[K+].[K+].Cl.[C:34](=[NH:39])(OCC)[CH3:35].Cl>P([O-])([O-])([O-])=O>[C:34]([N:19]1[CH2:20][C@@H:16]([S:15][C:7]2[C@H:6]([CH3:26])[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])[CH2:17][C@H:18]1[CH2:21][O:22][CH2:23][CH2:24][OH:25])(=[NH:39])[CH3:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 67866965HCID 67866965, compound

Product 1

HCID 18641567HCID 18641567, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

A solution of (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(2S,4S)-2-(2-hydroxyethyloxymethyl)pyrrolidin-4-ylthio]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (300 mg) in 0.05M phosphate buffer (pH 7, 30 ml) was adjusted to pH 8.5 with 30% potassium carbonate at 0° C., and ethyl acetimidate hydrochloride (3 g) was added in portions, while adjusting the mixture to around pH 8.5. After stirring for 1 hour, the reaction mixture was neutralized with 1N hydrochloric acid and washed with ethyl acetate and concentrated in vacuo. The residue was chromatographed on nonionic adsorption resin "Diaion HP-20" eluting successively with water and 5% aqueous acetone. The fractions containing the desired compound were collected and lyophilized to give (4R,5S,6S)-3-[(2S,4S)-1-acetimidoyl-2-(2-hydroxyethyloxymethyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]- 4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (290 mg).

Workup

  1. washwashed with ethyl acetate
  2. concentrationconcentrated in vacuo
  3. customThe residue was chromatographed on nonionic adsorption resin "Diaion
  4. wash" eluting successively with water and 5% aqueous acetone
  5. additionThe fractions containing the desired compound
  6. customwere collected

Sources & evidence

ORD record
ord-3fee159cf04141eeb2ad863f9fb88c22
Source dataset
uspto-grants-1991_10
Patent number
US05061804

Reaction notes

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