Hydrochloric Acid → 4'-Methyl-5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)biphenyl-3-carboxylic acid

HRID 1257551Notes

Reaction equation

HRID 1257551 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH2:21][C:17]4([CH2:20][CH2:19][CH2:18]4)[O:16][N:15]=3)[CH:11]=[C:10]([C:22]([O:24]C(C)(C)C)=[O:23])[CH:9]=2)=[CH:4][CH:3]=1.Cl>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH2:21][C:17]4([CH2:18][CH2:19][CH2:20]4)[O:16][N:15]=3)[CH:11]=[C:10]([C:22]([OH:24])=[O:23])[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66895976Tert-butyl 4'-methyl-5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)biphenyl-3-carboxylate

Product 1

HCID 668957974'-Methyl-5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)biphenyl-3-carboxylic acidYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4′-methyl-5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)biphenyl-3-carboxylate (1.26 g, 3.34 mmol) in dichloromethane (12 mL) was added hydrogen chloride (4.0 M in dioxane; 4.17 mL, 16.7 mmol). The reaction mixture was stirred at ambient temperature. After 18 h, the mixture was concentrated. Dichloromethane was added and the suspension was filtered. The solid cake was washed with dihchloromethane and dried under reduced pressure gave the title compound (1.0 g). MS 322.2 (M+1).

Workup

  1. concentrationthe mixture was concentrated
  2. additionDichloromethane was added
  3. filtrationthe suspension was filtered
  4. washThe solid cake was washed with dihchloromethane
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-a840c02afe6f405d80f373de8b4de5aa
Source dataset
uspto-grants-2013_06
Patent number
US08461185B2

Reaction notes

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