Hydrochloric Acid → HCID 58737080, compound

HRID 720164Notes

Reaction equation

HRID 720164 reaction equation
C[O:2][C:3](=[O:38])[CH:4]([N:16]1[CH2:21][CH2:20][N:19]([C:22](=[O:33])[CH:23]([NH2:32])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH:18]([CH2:34][CH:35]=[CH2:36])[C:17]1=[O:37])[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1.CO.[Li+].[OH-].Cl>C1COCC1.O>[CH2:34]([C@@H:18]1[N:19]([C:22](=[O:33])[C@H:23]([NH2:32])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:20][CH2:21][N:16]([C@@H:4]([CH2:5][C:6]2[CH:15]=[CH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]=2)[C:3]([OH:38])=[O:2])[C:17]1=[O:37])[CH:35]=[CH2:36]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 695877082-{3-Allyl-4-[2-amino-3-(4-fluorophenyl)propionyl]-2-oxo-piperazin-1-yl}-3-naphthalen-2-yl-propionic acid methyl ester

Product 1

HCID 58737080HCID 58737080, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{3-allyl-4-[2-amino-3-(4-fluorophenyl)propionyl]-2-oxo-piperazin-1-yl}-3-naphthalen-2-yl-propionic acid methyl ester, 10, (168 mg, 0.324 mmol) in a mixture of THF (1 mL)/CH3OH (0.5 mL)/H2O (0.5 mL) is added LiOH (43 mg, 1.78 mmol). The reaction mixture is stirred for 3 hours, acidified with 1N HCl to pH 3 and extracted with EtOAc. The extract is dried over Na2SO4, filtered, concentrated and dried under high vacuum to afford the desired product in quantitative yield.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe extract is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-aa1109470b374efa80b879910f2aaf06
Source dataset
uspto-grants-2006_11
Patent number
US07132539B2

Reaction notes

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