Methanol → HCID 131722256, compound

HRID 565136Notes

Reaction equation

HRID 565136 reaction equation
C([NH:8][C:9]1[C:10](=[CH:21][C:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:23][CH:24]=1)[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])(OC(C)(C)C)=O.Cl.C(OCC)(=O)C.CO.C([Cl:45])(=O)C>C(OCC)(=O)C>[ClH:45].[CH2:26]([O:25][C:22]1[CH:21]=[C:10]([C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[C:9]([NH2:8])=[CH:24][CH:23]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6367Acetyl chlorideHCID 15520892HCID 15520892, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 131722256HCID 131722256, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-Boc-5-benzyloxyanthranilic acid, benzyl ester (70 g, 161 mmol) was added to a 1.4 M HCl/ethyl acetate solution (prepared by the addition of methanol to acetyl chloride and subsequent dilution with ethyl acetate). The reaction mixture was stirred at room temperature for 21 hours. After cooling to 0° C., the reaction was gently stirred for an additional 2 hours. The crystalline product was filtered off and washed with 50 ml of cold ethyl acetate. Trace solvents were removed under high vacuum to yield 5-benzyloxyanthranilic acid, benzyl ester, hydrochloride (53.4 g, 86% yield).

Workup

  1. temperatureAfter cooling to 0° C.
  2. stirringthe reaction was gently stirred for an additional 2 hours
  3. filtrationThe crystalline product was filtered off
  4. washwashed with 50 ml of cold ethyl acetate
  5. customTrace solvents were removed under high vacuum

Sources & evidence

ORD record
ord-ed6f76a9006b44f287369cc529dfddad
Source dataset
uspto-grants-2001_01
Patent number
US06171578B2

Reaction notes

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