HCID 90282021, compound → HCID 89451884, compound

HRID 1497524Notes

Reaction equation

HRID 1497524 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([NH:19][CH2:20][C:21]2[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=2[C:23]([O:25]C)=[O:24])=[O:18])=[C:11]([Cl:31])[CH:10]=1)(C(C)(C)C)(C)C>Cl>[Cl:31][C:11]1[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][C:12]=1[CH2:15][CH2:16][C:17]([NH:19][CH2:20][C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[C:23]([OH:25])=[O:24])=[O:18]

Participants

3

Reactant 1

HCID 90282021HCID 90282021, compound

Product 1

HCID 89451884HCID 89451884, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of methyl 2-({[3-(4-{[tert-butyl(dimethyl)silyl]oxy}-2-chlorophenyl)propanoyl]amino}methyl)benzoate (460 mg) in concentrated hydrochloric acid (10.0 mL) was stirred at 50° C. for 4 days. The reaction mixture was concentrated under reduced pressure, then to the residue was added chloroform-methanol, and the insoluble material was separated by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform-methanol) to obtain 2-({[3-(2-chloro-4-hydroxyphenyl)propanoyl]amino}methyl)benzoic acid (140 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue was added chloroform-methanol
  3. customthe insoluble material was separated by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-5d4b7b40289441908f378bcc8b80197a
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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