Hydrochloric Acid → 2-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanine

HRID 276112Notes

Reaction equation

HRID 276112 reaction equation
C[O:2][C:3](=[O:30])[C@H:4]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[NH:5][C:6](=[O:21])[CH:7]([S:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[CH2:8][CH2:9][CH3:10].CO.[OH-].[Li+].Cl>CCCCCC.C(OCC)(=O)C.O1CCCC1>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][S:11][CH:7]([CH2:8][CH2:9][CH3:10])[C:6]([NH:5][C@H:4]([C:3]([OH:30])=[O:2])[CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 229508282-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanine methyl ester

Product 1

HCID 229508272-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine 2-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanine methyl ester (3.50 g, 8.15 mmol) and methanol (30 mL)and tetrahydrofuran (30 (mL). Cool in an ice bath. Add an aqueous 2M lithium hydroxide solution (8.2 mL, 16.4 mmol). After 18 hours, adjust the pH to about 6 using an aqueous 10% hydrochloric acid solution and evaporate in vacuo to give a residue. Partition the residue between dichloromethane and water, adjust the pH of the aqueous layer to about 1 using an aqueous 10% hydrochloric acid solution. Separate the layers, extract the aqueous layer repeatedly with ethyl acetate. Combine the organic layers, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 95% 1/1 hexane/ethyl acetate/5% acetic acid to give the title compound.

Workup

  1. temperatureCool in an ice bath
  2. customevaporate in vacuo
  3. customto give a residue
  4. customPartition the residue between dichloromethane and water
  5. customSeparate the layers
  6. extractionextract the aqueous layer repeatedly with ethyl acetate
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto give a residue

Sources & evidence

ORD record
ord-222d2ac6f50248dabfb0e58127fe60d6
Source dataset
uspto-grants-2002_03
Patent number
US06352976B1

Reaction notes

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