Hydrochloric Acid → HCID 20677584, compound

HRID 650584Notes

Reaction equation

HRID 650584 reaction equation
C[O:2][C:3](=[O:45])[C@@H:4]([NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37](=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([C:15]2[C:24]([CH3:25])=[CH:23][C:22]3[C:21]([CH3:27])([CH3:26])[CH2:20][CH2:19][C:18]([CH3:29])([CH3:28])[C:17]=3[CH:16]=2)[CH3:14])=[CH:8][CH:7]=1.[OH-].[Li+].Cl>C1COCC1.O>[C:37]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[NH:30][C@@H:4]([CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH:13]([C:15]2[C:24]([CH3:25])=[CH:23][C:22]3[C:21]([CH3:27])([CH3:26])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:29])[C:17]=3[CH:16]=2)[CH3:14])=[CH:10][CH:11]=1)[C:3]([OH:45])=[O:2])(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57238973HCID 57238973, compound

Product 1

HCID 20677584HCID 20677584, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S)-2-(2-Benzoylphenylamino)-3-(4(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphtalen-2-yl)-ethoxy)-phenyl)-propionic acid methyl ester (100 mg; 0.17 mmol) in THF (12 ml) was added a solution of lithium hydroxide (16 mg; 0.37 mmol) in water (8 ml). The reaction mixture was stirred at room temperature for 4 hours and 1 N HCl was added to pH 6. The mixture was extracted with methylene chloride (2×50 ml). The combined organic phases were dried and evaporated. The product was crystallized as the L-lysine salt from methanol-hexanes. Yield 95 mg. Compound 4.

Workup

  1. extractionThe mixture was extracted with methylene chloride (2×50 ml)
  2. customThe combined organic phases were dried
  3. customevaporated
  4. customThe product was crystallized as the L-lysine salt from methanol-hexanes

Sources & evidence

ORD record
ord-d1b7ac7e41534bd5bab28ad017af63b2
Source dataset
uspto-grants-2001_08
Patent number
US06274608B1

Reaction notes

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