Hydrochloric Acid → HCID 67435400, compound

HRID 1663405Notes

Reaction equation

HRID 1663405 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1([CH:12]2[C:25]3[C:20](=[N:21][C:22]([C:26]4[CH:35]=[CH:34][C:29]([C:30]([O:32]C)=[O:31])=[CH:28][CH:27]=4)=[CH:23][CH:24]=3)[O:19][C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:11][CH2:10][CH2:9]1)=[O:7])C.Cl>CO>[C:6]([C:8]1([CH:12]2[C:25]3[C:20](=[N:21][C:22]([C:26]4[CH:27]=[CH:28][C:29]([C:30]([OH:32])=[O:31])=[CH:34][CH:35]=4)=[CH:23][CH:24]=3)[O:19][C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:11][CH2:10][CH2:9]1)([OH:7])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67435429HCID 67435429, compound

Product 1

HCID 67435400HCID 67435400, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1 N aqueous solution of NaOH (5 mL, 5.00 mmol) was added to a solution of the product from Step 1 (250 mg, 0.564 mmol) in MeOH (10 mL) at room temperature. After 24 h at 80° C., the mixture was cooled to room temperature and adjusted pH2-3 with 1 N aqueous HCl. MeOH was evaporated in vacuo. The brown precipitate in the aqueous residue was collected by filtration and dried under vacuum to give 4-(5-(1-carboxycyclobutyl)-5H-chromeno[2,3-b]pyridin-2-yl)benzoic acid (210 mg, 93%). MS (ES+) m/z: 402 (M+H).

Workup

  1. customMeOH was evaporated in vacuo
  2. filtrationThe brown precipitate in the aqueous residue was collected by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-3b05af57151b465991eebb542850679f
Source dataset
uspto-grants-2011_10
Patent number
US08034940B2

Reaction notes

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