Hydrochloric Acid → 4-{1-[(S)-4-(2,3-Dihydro-benzo[1,4]dioxin-2-yl)-benzyl]-azetidin-3-yl}-benzoic acid

HRID 1842004Notes

Reaction equation

HRID 1842004 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:13][N:12]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C@@H:21]4[O:26][C:25]5[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=5[O:23][CH2:22]4)=[CH:17][CH:16]=3)[CH2:11]2)=[CH:6][CH:5]=1.O.[OH-].[Li+].Cl>O1CCOCC1.O>[O:26]1[C:25]2[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=2[O:23][CH2:22][C@@H:21]1[C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:12]2[CH2:13][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:31])=[O:2])=[CH:9][CH:8]=3)[CH2:11]2)=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 866953634-{1-[(S)-4-(2,3-Dihydro-benzo[1,4]dioxin-2-yl)-benzyl]-azetidin-3-yl}-benzoic acid methyl ester2×

Product 1

HCID 717371764-{1-[(S)-4-(2,3-Dihydro-benzo[1,4]dioxin-2-yl)-benzyl]-azetidin-3-yl}-benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-{1-[(S)-4-(2,3-Dihydro-benzo[1,4]dioxin-2-yl)-benzyl]-azetidin-3-yl}-benzoic acid methyl ester (prepared from Intermediate A and 4-Azetidin-3-yl-benzoic acid methyl ester according to General Method G) (504 mg, 1.21 mmol) and lithium hydroxide monohydrate (210 mg, 5.0 mmol) in 1,4-dioxane (10 mL) and water (1.0 mL) is stirred at 50° C. for 16 h. The mixture is neutralized with 1M HCl and concentrated. The residue is triturated with water to give the title compound 254 as a solid. (LC/MS method 16: ES+ m/z 402.5 [M+H]+, Rt=2.70 min)

Workup

  1. concentrationconcentrated
  2. customThe residue is triturated with water

Sources & evidence

ORD record
ord-d0934e387bdb4f449abccc596a3fb4c2
Source dataset
uspto-grants-2015_02
Patent number
US08946203B2

Reaction notes

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