4-Methylmorpholine → HCID 86737015, compound

HRID 1395823Notes

Reaction equation

HRID 1395823 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.Cl.C([S:39][C:40]([CH3:48])([CH3:47])[C@@H:41]([C:43]([O:45][CH3:46])=[O:44])[NH2:42])C1C=CC=CC=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([NH:42][C@H:41]([C:43]([O:45][CH3:46])=[O:44])[C:40]([SH:39])([CH3:48])[CH3:47])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 22811139HCID 22811139, compound

Product 1

HCID 86737015HCID 86737015, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

146 g of t-butoxycarbonyl proline are dissolved in 1500 ml of methylene chloride. 150 ml of N-methylmorpholine are added to the solution. The solution is cooled to -70° C. 89 ml of isobutylchloroformate are added. The reaction mixture is warmed to -15° C. and then cooled to -70° C. 197 g of methyl S-benzylpenicillaminate hydrochloride are added to the reaction mixture. The reaction mixture is stirred for sixteen hours at room temperature. The reaction mixture is extracted three times with 1.0 M potassium bisulfate and once with brine. The methylene chloride solution is dried over anhydrous sodium sulfate, filtered and stripped of solvent. The residue is dissolved in a minimum of diethyl ether. The ether solution is added to cold rapidly stirring hexane. The white precipitate is filtered and dried to afford the product, methyl t-butoxycarbonylprolylpenicillaminate.

Workup

  1. temperatureThe reaction mixture is warmed to -15° C.
  2. temperaturecooled to -70° C
  3. extractionThe reaction mixture is extracted three times with 1.0 M potassium bisulfate
  4. dry with materialThe methylene chloride solution is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. dissolutionThe residue is dissolved in a minimum of diethyl ether
  7. additionThe ether solution is added to cold rapidly stirring hexane
  8. filtrationThe white precipitate is filtered
  9. customdried

Sources & evidence

ORD record
ord-66125a0777354ca0bacba24d2caa6919
Source dataset
uspto-grants-1980_05
Patent number
US04204991

Reaction notes

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