Hydrochloric Acid → 3-Amino-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl ester di-hydrochloride salt

HRID 1245396Notes

Reaction equation

HRID 1245396 reaction equation
[ClH:1].[C:2]([O:6][C:7](=[O:35])[CH2:8][CH:9]([NH2:34])[CH:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=[C:25]([CH3:33])[CH:24]=3)=[CH:17][CH:16]=2)[CH2:11]1)(C)(C)C>CO>[ClH:1].[ClH:1].[CH3:2][O:6][C:7](=[O:35])[CH2:8][CH:9]([NH2:34])[CH:10]1[O:14][N:13]=[C:12]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=[C:25]([CH3:33])[CH:24]=3)=[CH:19][CH:20]=2)[CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 696401513-Amino-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid tert-butyl ester

Product 1

HCID 696397453-Amino-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl ester di-hydrochloride saltYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

HCl (g) was bubbled through a solution of the product from step 10d (0.3 g, 0.65 mmol) in methanol (20 mL) at room temperature for 5 minutes and the reaction was stirred for 3 h. This was complete, concentrated in vacuo to give a solid which was triturated into a powder with ethyl ether to give 3-amino-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl ester di-hydrochloride salt (0.21 g, 64%) as a off white solid. MS found: (M+H)+=420.

Workup

  1. concentrationThis was complete, concentrated in vacuo
  2. customto give a solid which
  3. customwas triturated into a powder with ethyl ether

Sources & evidence

ORD record
ord-75d27406e53745ac938baa2e5ca2cb24
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

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