Lithium hydroxide, monohydrate → HCID 9850300, compound

HRID 2270856Notes

Reaction equation

HRID 2270856 reaction equation
[Cl:1][C:2]1[CH:27]=[C:26]([C:28]([NH:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([OH:38])[CH:33]=2)=[O:29])[CH:25]=[C:24]([CH3:39])[C:3]=1[C:4]([NH:6][C@H:7]([C:20]([O:22]C)=[O:21])[CH2:8][NH:9][C:10](=[O:19])[C:11]1[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([OH:18])[CH:12]=1)=[O:5].O.[OH-].[Li+]>O1CCCC1.CO.O>[Cl:1][C:2]1[CH:27]=[C:26]([C:28]([NH:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([OH:38])[CH:33]=2)=[O:29])[CH:25]=[C:24]([CH3:39])[C:3]=1[C:4]([NH:6][C@H:7]([C:20]([OH:22])=[O:21])[CH2:8][NH:9][C:10](=[O:19])[C:11]1[CH:12]=[C:13]([OH:18])[CH:14]=[C:15]([OH:17])[CH:16]=1)=[O:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 131723041HCID 131723041, compound

Product 1

HCID 9850300HCID 9850300, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]-6-methylbenzoyl]-3-(3,5-dihydroxybenzoylamino)-L-alanine, methyl ester (790 mg, 0.87 mmol) in tetrahydrofuran/methanol (1:1; 8 mL) was added to a solution of lithium hydroxide monohydrate (183 mg, 4.4 mmol) in water (4 mL). The solution was stirred at room temperature overnight and then the solvents were evaporated. Water (15 mL) was added and the solution was acidified with 3 M HCl. The mixture was extracted with ethyl acetate (3×20 mL) and the combined extracts were washed with brine and evaporated. The residue was dissolved in methanol (14 mL) and purified in two portions by HPLC to give N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]-6-methylbenzoyl]-3-(3,5-dihydroxybenzoylamino)-L-alanine (65 mg, 14%).

Workup

  1. customthe solvents were evaporated
  2. additionWater (15 mL) was added
  3. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  4. washthe combined extracts were washed with brine
  5. customevaporated
  6. dissolutionThe residue was dissolved in methanol (14 mL)
  7. custompurified in two portions by HPLC

Sources & evidence

ORD record
ord-512b7b5262c24d3ab1cf2f1efe850d08
Source dataset
uspto-grants-2001_12
Patent number
US06331640B1

Reaction notes

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