Lithium hydroxide, monohydrate → HCID 60115128, compound

HRID 393074Notes

Reaction equation

HRID 393074 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([C:25](=[O:35])[CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[CH:29]=2)[CH:22]=[CH:21][C:3]=1[C:4]([NH:6][C@H:7]([C:17]([O:19]C)=[O:18])[CH2:8][NH:9][C:10]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)=[O:11])=[O:5].O.[OH-].[Li+]>O1CCCC1.CO.O>[Cl:1][C:2]1[CH:24]=[C:23]([C:25](=[O:35])[CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[CH:29]=2)[CH:22]=[CH:21][C:3]=1[C:4]([NH:6][C@H:7]([C:17]([OH:19])=[O:18])[CH2:8][NH:9][C:10]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)=[O:11])=[O:5]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 131723035HCID 131723035, compound

Product 1

HCID 60115128HCID 60115128, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of N-[2-chloro-4-[1-oxo-3-(3-hydroxyphenyl)propyl]benzoyl]-3-(thiophene-2-carbonyl)amino-L-alanine, methyl ester (120 mg, 0.23 mmol) and lithium hydroxide monohydrate (40 mg, 0.95 mmol) in tetrahydrofuran/methanol/water (2:2:1; 2.5 mL) was stirred at room temperature for 90 min. The solvent was evaporated, then water was added, followed by 1 M HCl (1.1 mL). The resulting solid was filtered off, washed with water, dried, and purified by HPLC to give N-[2-chloro-4-[1-oxo-3-(3-hydroxyphenyl)propyl]-benzoyl]-3-(thiophene-2-carbonyl)amino-L-alanine (95 mg, 81%).

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. filtrationThe resulting solid was filtered off
  4. washwashed with water
  5. customdried
  6. custompurified by HPLC

Sources & evidence

ORD record
ord-ee97c2254e2d46be8de82703cd9777de
Source dataset
uspto-grants-2004_10
Patent number
US06803384B2

Reaction notes

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