Hydrochloric Acid → Disodium

HRID 437356Notes

Reaction equation

HRID 437356 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([C:10]([OH:12])=[O:11])[C:7]([OH:9])=O.[NH2:13][CH:14]1[C:27](=[O:28])[N:16]2[CH:17]([P:22]([OH:26])([O:24][CH3:25])=[O:23])[C:18]([CH3:21])([CH3:20])[S:19][C@H:15]12.[OH-].[Na+:30].Cl.C(N=C=NCCCN(C)C)C.Cl.C(C(CCCC)C([O-])=O)C.[Na+:54]>C(OCC)(=O)C.O>[C:10]([CH:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C:7]([NH:13][CH:14]1[C:27](=[O:28])[N:16]2[CH:17]([P:22]([OH:26])([O:24][CH3:25])=[O:23])[C:18]([CH3:20])([CH3:21])[S:19][C@H:15]12)=[O:9])([OH:12])=[O:11].[Na:30][Na:54]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15607089(Thiophen-2-yl)propanedioic acidHCID 23672331Sodium 2-ethylhexanoateHCID 867348606-amino-2,2-dimethyl-3-(O-methylphosphono)penam

Product 2

HCID 141233DisodiumHCID 867348626-[2-carboxy-2-(2-thienyl)acetamido]-2,2-dimethyl-3-(O-methylphosphono)penam

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 370 mg. (0.002 mole) of 2-(2-thienyl)-malonic acid (Netherlands Patent No. 6805524) in 4 ml. of water is added 532 mg. (0.002 mole) of 6-amino-2,2-dimethyl-3-(O-methylphosphono)penam. The pH is then adjusted to 6.5 using 20% aqueous sodium hydroxide. The resulting solution is cooled to 0° C. and 384 mg. (0.002 mole) of 1-ethyl-3-(3-dimethylaminoprop-1-yl)carbodiimide hydrochloride is added. The solution is stirred for 3.5 hours at 0° C., with a pH maintained between 6 and 7 using 1N hydrochloric acid. At this point, the pH of the solution is then lowered to 2.0 and the mixture is extracted with two 30 ml. portions of ethyl acetate. The combined extracts are dried, and are then concentrated to about 15 ml. To this solution is added a solution of 665 mg. (0.004 mole) of sodium 2 -ethylhexanoate in 2.6 ml. of ethyl acetate. The solid which precipitates is filtered, and dried to give 6-[2-carboxy-2-(2-thienyl)acetamido]-2,2-dimethyl-3-(O-methylphosphono)penam as its disodium salt.

Workup

  1. additionTo a stirred suspension of 370 mg
  2. extractionthe mixture is extracted with two 30 ml
  3. customThe combined extracts are dried
  4. concentrationare then concentrated to about 15 ml
  5. additionTo this solution is added a solution of 665 mg
  6. customThe solid which precipitates
  7. filtrationis filtered
  8. customdried

Sources & evidence

ORD record
ord-a8e50d9c0eae4ce7883b0f1075b02859
Source dataset
uspto-grants-1977_06
Patent number
US04031077

Reaction notes

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