Lithium Hydroxide → HCID 53926717, compound

HRID 1976960Notes

Reaction equation

HRID 1976960 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:47])[C@H:6]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37]([C:39]2[C:44]([Cl:45])=[CH:43][CH:42]=[CH:41][C:40]=2[Cl:46])=[O:38])=[CH:32][CH:31]=1)[NH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=2)(=[O:18])=[O:17])=[CH:12][C:11]=1[Cl:28])=[O:9]>CO.O1CCCC1>[Cl:46][C:40]1[CH:41]=[CH:42][CH:43]=[C:44]([Cl:45])[C:39]=1[C:37]([NH:36][C:33]1[CH:32]=[CH:31][C:30]([CH2:29][C@@H:6]([C:5]([OH:47])=[O:4])[NH:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=3)(=[O:18])=[O:17])=[CH:12][C:11]=2[Cl:28])=[O:9])=[CH:35][CH:34]=1)=[O:38]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 541912724-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]sulfonyl]phenyl]carbonyl]-L-phenylalanine methyl ester

Product 1

HCID 53926717HCID 53926717, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

An aqueous 1N lithium hydroxide solution (0.25 mL) was added to a solution of 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]sulfonyl]phenyl]carbonyl]-L-phenylalanine methyl ester (51 mg; 0.0738 mmol) in methanol (0.5 mL) and tetrahydrofuran (0.35 mL). After the reaction was stirred at room temperature for 90 minutes, the solvents were removed under reduced pressure. The crude product in the minimum amount of methanol was then applied to a column of silica eel (5 g) made up in a mixture of chloroform, methanol, acetic acid and water (15:3:1:0.6). The column was eluted with the same solvent mixture and the appropriate fractions were combined and evaporated. The residue was lyophilized from deionized water to give 36 mg of 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]sulfonyl]phenyl]carbonyl]-L-phenylalanine as an off white solid. FAB HRMS: (C30H24Cl3N3O7S) Obs. Mass 676.0482 Calcd. Mass 676.0479 (M+H).

Workup

  1. customthe solvents were removed under reduced pressure
  2. additionmade up in a mixture of chloroform, methanol, acetic acid and water (15:3:1:0.6)
  3. washThe column was eluted with the same solvent mixture
  4. customevaporated

Sources & evidence

ORD record
ord-02c2f426bfc64ec4b143beb2f9343ff6
Source dataset
uspto-grants-2001_05
Patent number
US06229011B1

Reaction notes

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