Hydrochloric Acid → HCID 10457723, compound

HRID 860956Notes

Reaction equation

HRID 860956 reaction equation
[OH-].[Li+].C[N:4]([C:9](=[O:30])[C:10]1[CH:15]=[C:14]([Cl:16])[C:13]([O:17][C:18]2[CH:23]=[C:22]([CH:24]([CH3:26])[CH3:25])[C:21]([OH:27])=[C:20]([Br:28])[CH:19]=2)=[C:12]([Cl:29])[CH:11]=1)[CH2:5][C:6]([OH:8])=[O:7].Cl>O1CCCC1>[Cl:16][C:14]1[CH:15]=[C:10]([CH:11]=[C:12]([Cl:29])[C:13]=1[O:17][C:18]1[CH:23]=[C:22]([CH:24]([CH3:26])[CH3:25])[C:21]([OH:27])=[C:20]([Br:28])[CH:19]=1)[C:9]([NH:4][CH2:5][C:6]([OH:8])=[O:7])=[O:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69385037HCID 69385037, compound

Product 1

HCID 10457723HCID 10457723, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (1 N, 9 mL) was added at room temperature to a mixture of methyl-N-[3,5-dichloro-4-(3-bromo-4-hydroxy-5-isopropylphenoxy)benzoyl]glycine (150 mg, 0.305 mmol) and tetrahydrofuran (9 mL). After 16 hours, the reaction mixture was acidified with hydrochloric acid (1 N) and extracted with ethyl acetate. Filtration through a pad of silica gave N-[3,5-dichloro-4-(3-bromo-4-hydroxy-5-isopropylphenoxy)benzoyl]-glycine in quantitative yield as a light yellow solid. LC-MS (ES−1): m/z 476.

Workup

  1. extractionextracted with ethyl acetate
  2. filtrationFiltration through a pad of silica

Sources & evidence

ORD record
ord-9213d1a273994016881325805eb58f08
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

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