Hydrochloric Acid → HCID 89462624, compound

HRID 1473265Notes

Reaction equation

HRID 1473265 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:11]([C:12]([O:14]C)=[O:13])=[C:10]([C:16]([O:18]C)=[O:17])[C:9]3[CH2:20][O:21][CH2:22][CH2:23][C:8]2=3)=[CH:4][CH:3]=1.[OH-].[K+].Cl>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]([C:12]([OH:14])=[O:13])=[C:10]([C:16]([OH:18])=[O:17])[C:9]3[CH2:20][O:21][CH2:22][CH2:23][C:8]2=3)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 89462640HCID 89462640, compound

Product 1

HCID 89462624HCID 89462624, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of dimethyl 1-(4-fluorobenzyl)-1,4,6,7-tetrahydropyrano[4,3-b]pyrrole-2,3-dicarboxylate (3.92 g, 11.29 mmol) and KOH (3.17 g, 56.4 mmol) in Ethanol (113 ml) was heated to 90° C. After 18 h, the reaction mixture was poured into 1M HCl and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated in vacuo to afford 1-(4-fluorobenzyl)-1,4,6,7-tetrahydropyrano[4,3-b]pyrrole-2,3-dicarboxylic acid (3.1 g, 9.71 mmol, 86% yield). LCMS (m/z) ES+=320 (M+1).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2bfec46287d74881983c2f312ca39de7
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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