Acetic Acid → HCID 18606079, compound

HRID 979835Notes

Reaction equation

HRID 979835 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:29])[C@H:12]([CH3:28])[NH:13][C@H:14]([C:23]([O:25]CC)=[O:24])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)C.C(O)CCC.O.C(O)(=O)C>C(O)C.[OH-].[Na+]>[C:23]([C@@H:14]([NH:13][C@H:12]([C:11]([N:7]1[CH2:8][CH2:9][CH2:10][C@H:6]1[CH2:5][C:4]([OH:30])=[O:3])=[O:29])[CH3:28])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([OH:25])=[O:24]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 2631-ButanolHCID 962WaterHCID 54473112HCID 54473112, compound

Product 1

HCID 18606079HCID 18606079, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl-(S)-2-pyrrolidineacetic acid ethyl ester (87 mg; 0.21 mmol) in 1 ml of ethanol and 1 ml of 1.0N sodium hydroxide was stirred overnight at room temperature. The mixture was concentrated under reduced pressure to remove ethanol, neutralized with dilute hydrochloric acid and poured onto a 80×12 mm column of Dowex 50W×4 ion exchange resin (H+ cycle). The column was eluted with 200 ml water followed by 100 ml of 2.5% pyridine in water. Evaporation under reduced pressure of the aqueous pyridine eluate gave the product desired as a white crystalline solid (72 mg) ms M+ 362; TLC Rf 0.57-silica gel 4:1:1-n-butanol:water:acetic acid;

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto remove ethanol
  3. additionpoured onto a 80×12 mm column of Dowex 50W×4 ion exchange resin (H+ cycle)
  4. washThe column was eluted with 200 ml water
  5. customEvaporation under reduced pressure of the aqueous pyridine eluate
  6. customgave the product

Sources & evidence

ORD record
ord-e83b65b378f94a53abceae5b5d0988e0
Source dataset
uspto-grants-1987_01
Patent number
US04634716

Reaction notes

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