Hydrochloric Acid → HCID 54040558, compound

HRID 620802Notes

Reaction equation

HRID 620802 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]([CH3:29])[C:7]([S:15][C@@H:16]1[CH2:20][NH:19][C@H:18]([CH2:21][O:22][CH2:23][CH2:24][NH:25][C:26]([NH2:28])=[O:27])[CH2:17]1)=[C:8]2[C:12]([OH:14])=[O:13])[CH3:3].Cl.[C:31](=[NH:36])(OCC)[CH3:32].C(=O)([O-])[O-].[K+].[K+].Cl>O>[C:31]([N:19]1[CH2:20][C@@H:16]([S:15][C:7]2[C@H:6]([CH3:29])[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][NH:25][C:26]([NH2:28])=[O:27])(=[NH:36])[CH3:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 54369112HCID 54369112, compound

Product 1

HCID 54040558HCID 54040558, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(2S,4S)-2-{(2-ureidoethyl)oxymethyl}-pyrrolidin-4-yl]thio-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.15 g) in water (30 ml) was added ethyl acetimidate hydrochloride (1.65 g) by portions at 0°-5° C., keeping the pH between 8.4-8.6 with 10% aqueous potassium carbonate. After adjusting to pH 6.5 with lN aqueous hydrochloric acid, the solution was washed with 10% solution of tetrahydrofuran in ethyl acetate (50 ml) by four portions and the organic solvent was removed by evaporation. The residual solution was subjected to a column chromatography on nonionic adsorption resin, "HP-20" (30 ml), washed with water, eluted with 5% aqueous isopropyl alcohol and lyophilized to give (4R,5S,6S)-3-[(2S,4S)-1-acetimidoyl-2-{(2-ureidoethyl)oxymethyl}pyrrolidin-4-yl]thio-6-[ (1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.11 g).

Workup

  1. washthe solution was washed with 10% solution of tetrahydrofuran in ethyl acetate (50 ml) by four portions
  2. customthe organic solvent was removed by evaporation
  3. washwashed with water
  4. washeluted with 5% aqueous isopropyl alcohol

Sources & evidence

ORD record
ord-118af1820637447fa02424bca29a13b9
Source dataset
uspto-grants-1989_04
Patent number
US04822787

Reaction notes

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