Hydrochloric Acid → 4-[6-(Cyclopentyloxycarbonyl)amino-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl]-3-methoxybenzoic acid

HRID 1080773Notes

Reaction equation

HRID 1080773 reaction equation
O.[OH-].[Li+].[CH:4]1([O:9][C:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]3[O:21][CH2:20][CH2:19][N:18]([CH2:22][C:23]4[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][C:24]=4[O:33][CH3:34])[C:17]=3[CH:35]=2)=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5]1.Cl>CO.O>[CH:4]1([O:9][C:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]3[O:21][CH2:20][CH2:19][N:18]([CH2:22][C:23]4[CH:32]=[CH:31][C:26]([C:27]([OH:29])=[O:28])=[CH:25][C:24]=4[O:33][CH3:34])[C:17]=3[CH:35]=2)=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 14763127Methyl 4-[6-(cyclopentyloxycarbonyl) amino-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl]-3-methoxybenzoate

Product 1

HCID 147631294-[6-(Cyclopentyloxycarbonyl)amino-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl]-3-methoxybenzoic acidYield 67.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Lithium hydroxide monohydrate (0.267 g.) was added as a solid to a stirred solution of methyl 4-[6-(cyclopentyloxycarbonyl)amino-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl]-3-methoxybenzoate (0.7 g.) in methanol (15 ml.) and water (2 ml.). The mixture was stirred for 12 hours then diluted with water and acidified to pH 3.35 with 3M hydrochloric acid. The precipitate which formed was isolated by filtration, washed with water and crystallized from methanol to give the title compound as a solid (0.457 g., 67%), m.p. 221°-222° C.

Workup

  1. customThe precipitate which formed
  2. customwas isolated by filtration
  3. washwashed with water
  4. customcrystallized from methanol

Sources & evidence

ORD record
ord-5546bb6d9f6643f2a67c3fc5df862106
Source dataset
uspto-grants-1996_12
Patent number
US05583152

Reaction notes

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