Hydrochloric Acid → HCID 66932294, compound

HRID 518228Notes

Reaction equation

HRID 518228 reaction equation
C[O:2][C:3](=[O:30])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]2[O:27][C:13]3([CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:15][CH2:14]3)[NH:12][C:11](=[O:28])[C:10]=2[CH:29]=1.[OH-].[Na+].Cl>O1CCOCC1.O>[C:21]1([CH2:20][CH2:19][N:16]2[CH2:15][CH2:14][C:13]3([NH:12][C:11](=[O:28])[C:10]4[CH:29]=[C:6](/[CH:5]=[CH:4]/[C:3]([OH:30])=[O:2])[CH:7]=[CH:8][C:9]=4[O:27]3)[CH2:18][CH2:17]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66932261HCID 66932261, compound

Product 1

HCID 66932294HCID 66932294, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

(E)-3-{1′-(2-Phenyl-ethyl)-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4′-piperidin]-6-yl}-acrylic acid methyl ester (292 mg, 0.719 mmol) was suspended in dioxane (5 ml) and water (5 ml). 1 M NaOH (0.93 ml) was added and the resulting mixture was stirred overnight at RT. The mixture was neutralized with 1 M HCl and concentrated under vacuum. The pH was brought to 4 with 1 M HCl and the resulting solid was decanted and dried to give (E)-3-{1′-(2-phenyl-ethyl)-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4′-piperidin]-6-yl}-acrylic acid (265 mg).

Workup

  1. concentrationconcentrated under vacuum
  2. customthe resulting solid was decanted
  3. customdried

Sources & evidence

ORD record
ord-83c2b136538945109f77696843431733
Source dataset
uspto-grants-2015_08
Patent number
US09115148B2

Reaction notes

Loading…