Hydrochloric Acid → HCID 44539532, compound

HRID 1969084Notes

Reaction equation

HRID 1969084 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:22])[CH3:21])=[CH:15][C:14]=2[CH2:23][N:24]([C:34]([O:36][CH3:37])=[O:35])[C@@H:25]([CH3:33])[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:7]=1)C.[OH-].[Li+].Cl>C1COCC1>[C:20]([NH:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:8]2[CH:7]=[C:6]([CH2:5][C:4]([OH:38])=[O:3])[CH:11]=[CH:10][CH:9]=2)=[C:14]([CH2:23][N:24]([C:34]([O:36][CH3:37])=[O:35])[C@@H:25]([CH3:33])[CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:15]=1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58288531HCID 58288531, compound

Product 1

HCID 44539532HCID 44539532, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To [3-(4-acetylamino-2-{[methoxycarbonyl-((S)-1-methyl-2-phenyl-ethyl)-amino]-methyl}-phenoxy)-phenyl]-acetic acid ethyl ester (0.048 g, 0.09 mmol) in THF (2 mL) was added 1N aqueous lithium hydroxide (2 mL), and the reaction was stirred over the weekend at room temperature. Once no starting material was seen by analytical LCMS, the mixture was acidified with 1N aqueous HCl and extracted with EtOAc. The combined organic layers were dried and concentrated, and the residue was purified by preparative HPLC and converted to the free base with saturated aqueous NaHCO3 to give the title compound. M+H=491.

Workup

  1. extractionextracted with EtOAc
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-1b34ea58803349fc80e245a042c04736
Source dataset
uspto-grants-2013_04
Patent number
US08426449B2

Reaction notes

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