Lithium Hydroxide → HCID 178453480, compound

HRID 2269532Notes

Reaction equation

HRID 2269532 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:49])([CH3:48])[C:10]([NH:12][C@H:13]([CH2:38][C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[NH:41][CH:40]=1)[C:14]([NH:16][C:17]1[N:18]=[C:19]([CH:22]([C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=2)[C:23]([O:25]CC)=[O:24])[NH:20][CH:21]=1)=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].O1CCOCC1>O>[C:1]([O:5][C:6]([NH:8][C:9]([CH3:49])([CH3:48])[C:10]([NH:12][C@H:13]([CH2:38][C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[NH:41][CH:40]=1)[C:14]([NH:16][C:17]1[N:18]=[C:19]([CH:22]([C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=2)[C:23]([OH:25])=[O:24])[NH:20][CH:21]=1)=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 178470590HCID 178470590, compound

Product 1

HCID 178453480HCID 178453480, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution consisting of ethyl 2-[4-((2R)-2-{2-[(tert-butoxy)carbonylamino]-2-methylpropanoylamino}-3-indol-3-ylpropanoylamino)imidazolyl]-2-(2-naphthyl)acetate (1.52 grams, 2.28 mmol), lithium hydroxide (0.11 grams, 4.56 mmol), dioxane (10 mL), and water (10 mL) was stirred at ambient temperature until complete as determined by hplc (30 minutes). The reaction mixture was concentrated to dryness and the residue was dissolved in water (20 mL). The aqueous solution was adjusted to a pH of 3 using a 10% sodium bisulfate solution and extracted with ethyl acetate (3×25 mL). The organic layers were combined, dried using sodium sulfate, filtered, and concentrated to give 1.34 grams (92%) of 2-[4-((2R)-2-{2-[(tert-butoxy)carbonylamino]-2-methylpropanoylamino}-3-indol-3-ylpropanoylamino)imidazolyl]-2-(2-naphthyl)acetic acid.

Workup

  1. customas determined by hplc (30 minutes)
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutionthe residue was dissolved in water (20 mL)
  4. extractionextracted with ethyl acetate (3×25 mL)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2b52e188f94642468c815997a44b4a34
Source dataset
uspto-grants-2001_12
Patent number
US06329342B1

Reaction notes

Loading…