Hydrochloric Acid → HCID 23003912, compound

HRID 396713Notes

Reaction equation

HRID 396713 reaction equation
[C:1]([NH:4][C@@H:5]([CH2:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21](=[O:42])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH3:39])=[O:31])=[C:25]([O:40][CH3:41])[CH:24]=1)[CH2:16][CH2:15][CH2:14]2)[C:6]([O:8]C)=[O:7])(=[O:3])[CH3:2].O.[OH-].[Li+].Cl>O1CCOCC1.O>[C:1]([NH:4][CH:5]([CH2:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21](=[O:42])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH3:39])=[O:31])=[C:25]([O:40][CH3:41])[CH:24]=1)[CH2:16][CH2:15][CH2:14]2)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86759117HCID 86759117, compound

Product 1

HCID 23003912HCID 23003912, compoundYield 9.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl (S) 2-acetylamino-3-(1-{[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetyl}-1,2,3,4-tetrahydro-quinolin-6-yl)-propionate [220 mg, Reference Example 4(1)] in dioxane (3 ml) was treated with a solution of lithium hydroxide hydrate (50 mg) in water (1 ml). The mixture was stirred at room temperature for 3 hours, then treated with water (5 ml), then acidified to pH 1-2 by the addition of dilute hydrochloric acid (with ice cooling). The resulting precipitate was extracted three times with ethyl acetate and the combined extracts were washed with water, then with brine, then dried and then evaporated. The residue was recrystallised from ethyl acetate to give the title compound (21 mg)as a white powder. LC-MS: RT=2.77 minutes (100% total area by ELS); MS (ES+) 581 (MNa+).

Workup

  1. extractionThe resulting precipitate was extracted three times with ethyl acetate
  2. washthe combined extracts were washed with water
  3. dry with materialwith brine, then dried
  4. customevaporated
  5. customThe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-d1591500d6184b899796dc28985f0dd5
Source dataset
uspto-grants-2003_08
Patent number
US06608084B1

Reaction notes

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