Lithium Hydroxide → HCID 178453480, compound

HRID 2306768Notes

Reaction equation

HRID 2306768 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-methyl propanoylamino}-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-a9f96c89f0f54aa2aeb8ad5470b29705
Source dataset
uspto-grants-2004_12
Patent number
US06828331B1

Reaction notes

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