Hydrochloric Acid → HCID 71075520, compound

HRID 2170709Notes

Reaction equation

HRID 2170709 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C@@H:11]([NH:13][C:14]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[N:21]([CH2:25][C:26]2[CH:27]=[C:28]([CH:36]=[CH:37][CH:38]=2)[O:29][C@@H:30]([CH3:35])[C:31]([O:33]C)=[O:32])[C:20]([CH3:39])=[C:19]3[CH3:40])=[O:15])[CH3:12])[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C@@H:11]([NH:13][C:14]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[N:21]([CH2:25][C:26]2[CH:27]=[C:28]([CH:36]=[CH:37][CH:38]=2)[O:29][C@@H:30]([CH3:35])[C:31]([OH:33])=[O:32])[C:20]([CH3:39])=[C:19]3[CH3:40])=[O:15])[CH3:12])[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 71075489HCID 71075489, compound

Product 1

HCID 71075520HCID 71075520, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 2-(3-((5(((S)-1-(3-isopropoxyphenyl)ethyl) carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)phenoxy)propanoate (70 mg, 0.13 mmol, 1 equiv) in THF (2 mL) was added a 1 N LiOH aqueous solution of (1 mL). The reaction mixture was stirred 6 h at room temperature, then acidified with a 0.5 N HCl aqueous solution. The mixture was filtered and the precipate was dissolved in methanol and concentrated to obtain the crude product which was purified by prep. HPLC (MeOH/Acetonitrile/water 0.1% TFA) to obtain the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. dissolutionthe precipate was dissolved in methanol
  3. concentrationconcentrated
  4. customto obtain the crude product which
  5. customwas purified by prep

Sources & evidence

ORD record
ord-b573e63655d04466ad0e409b19641a9d
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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