Hydrochloric Acid → HCID 21905747, compound

HRID 1247257Notes

Reaction equation

HRID 1247257 reaction equation
Cl.C([O:4][C:5](=[O:33])[CH2:6][O:7][C:8]1[CH:13]=[C:12]([CH:14]([C:18](=[O:30])[NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27](=[NH:29])[NH2:28])=[CH:23][CH:22]=2)[O:15][CH2:16][CH3:17])[CH:11]=[CH:10][C:9]=1[O:31][CH3:32])C.O.[OH-].[Na+].Cl>C1COCC1>[C:27]([C:24]1[CH:23]=[CH:22][C:21]([CH2:20][NH:19][C:18]([CH:14]([O:15][CH2:16][CH3:17])[C:12]2[CH:11]=[CH:10][C:9]([O:31][CH3:32])=[C:8]([CH:13]=2)[O:7][CH2:6][C:5]([OH:33])=[O:4])=[O:30])=[CH:26][CH:25]=1)(=[NH:28])[NH2:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 69289053HCID 69289053, compound

Product 1

HCID 21905747HCID 21905747, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of (RS)-{5-[(4-carbamimidoyl-benzylcarbamoyl)-ethoxy-methyl]-2-methoxy-phenoxy}-acetic acid ethyl ester hydrochloride (example 18.5, 0.045 g) at rt in THF (1 ml) and water (0.5 ml) was added 1.0 N NaOH (0.2 ml). The mixture was then stirred at rt under an argon atmosphere for 3 h. The mixture waa acidified to pH 5–6 by addition of 1.0 N HCl. The THF was removed (rotavapor) and the product precipitated out from the remaining water. It was collected by filtration, washed with water and cyclohexane and dried overnight under high vacuum to give (RS)-{5-[(4-carbamimidoyl-benzylcarbamoyl)-ethoxy-methyl]-2-methoxy-phenoxy}-acetic acid (0.027 g) as a white powder. MS 416.3 ([M+H]+)

Workup

  1. customThe THF was removed (rotavapor)
  2. customthe product precipitated out from the remaining water
  3. filtrationIt was collected by filtration
  4. washwashed with water and cyclohexane
  5. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-5237428d394c44709d80eb30146f202b
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

Loading…