Sodium Hydroxide → HCID 15117447, compound

HRID 1029691Notes

Reaction equation

HRID 1029691 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]([C@@H:15]1[CH2:19][CH2:18][NH:17][CH2:16]1)=[C:8]2[C:12]([OH:14])=[O:13])[CH3:3].Cl.[C:21](=[NH:26])(OCC)[CH3:22].[OH-].[Na+]>O>[C:21]([N:17]1[CH2:18][CH2:19][C@@H: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:26])[CH3:22]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 15117375HCID 15117375, compound

Product 1

HCID 15117447HCID 15117447, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(3S)-pyrrolidin-3-yl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (1.0 g) in water (30 ml) was added ethyl acetimidate hydrochloride (2.8 g) at 0° C while adjusting pH to 8.5 with 30% sodium hydroxide solution. After stirring for 30 minutes at the same temperature, the solution was adjusted to pH 6.5 with lN-hydrochloric.acid, washed with ethyl acetate, and then concentrated in vacuo. The residue was chromatographed on nonionic adsorption resin "Diaion HP-20" eluting with aqueous isopropyl alcohol (3%). The farctions containing the desired compound were collected and lyophilized to give (5R,6S)-3-[(3S)-1-acetimidoylpyrrolidin-3-yl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (550 mg).

Workup

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

Sources & evidence

ORD record
ord-848487e1da234331af0def8323e2533d
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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