Methyl 2-benzamido-2-(4-methoxycarbonyl-3-methoxy-6-methylphenyl)acetate → 4-(amino-carboxy-methyl)-2-hydroxy-5-methyl-benzoic Acid

HRID 343953Notes

Reaction equation

HRID 343953 reaction equation
C([NH:9][CH:10]([C:15]1[C:20]([CH3:21])=[CH:19][C:18]([C:22]([O:24]C)=[O:23])=[C:17]([O:26]C)[CH:16]=1)[C:11]([O:13]C)=[O:12])(=O)C1C=CC=CC=1>Cl>[C:22]([C:18]1[CH:19]=[C:20]([CH3:21])[C:15]([CH:10]([C:11]([OH:13])=[O:12])[NH2:9])=[CH:16][C:17]=1[OH:26])([OH:24])=[O:23]

Participants

3

Reactant 1

HCID 54245466Methyl 2-benzamido-2-(4-methoxycarbonyl-3-methoxy-6-methylphenyl)acetate

Product 1

HCID 100365994-(amino-carboxy-methyl)-2-hydroxy-5-methyl-benzoic Acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred suspension of methyl 2-benzamido-2-(4-methoxycarbonyl-3-methoxy-6-methylphenyl)acetate (120 mg, 0.32 mmol) in aqueous hydrochloric acid (5M, 3 ml) was heated to 110° C. for 7 days in a PTFE lined stainless steel sealed reaction vessel. The contents were periodically cooled, evaporated and topped up with an equivalent amount of fresh aqueous hydrochloric acid. The contents were cooled and chromatographed on ion exchange resin following the procedure described in Example 1 (iii) to give the title compound as an off-white solid, m.p. >250° C.

Workup

  1. customsealed
  2. customreaction vessel
  3. temperatureThe contents were periodically cooled
  4. customevaporated
  5. temperatureThe contents were cooled
  6. customchromatographed on ion exchange resin

Sources & evidence

ORD record
ord-32942008bd02400897c07b71e116579d
Source dataset
uspto-grants-1999_01
Patent number
US05863947

Reaction notes

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