Sodium Hydroxide → (+/-)-(E)-3-{1'-methyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3'-piperidin]-6-yl}-acrylic acid

HRID 874313Notes

Reaction equation

HRID 874313 reaction equation
C[O:2][C:3](=[O:23])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]2[O:20][C:13]3([CH2:18][CH2:17][CH2:16][N:15]([CH3:19])[CH2:14]3)[NH:12][C:11](=[O:21])[C:10]=2[CH:22]=1.[OH-].[Na+]>O.O1CCOCC1>[CH3:19][N:15]1[CH2:16][CH2:17][CH2:18][C:13]2([NH:12][C:11](=[O:21])[C:10]3[CH:22]=[C:6](/[CH:5]=[CH:4]/[C:3]([OH:23])=[O:2])[CH:7]=[CH:8][C:9]=3[O:20]2)[CH2:14]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67071521(+/-)-(E)-3-{1'-Methyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3'-piperidin]-6-yl}-acrylic acid methyl ester

Product 1

HCID 67071585(+/-)-(E)-3-{1'-methyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3'-piperidin]-6-yl}-acrylic acidYield 98.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (±)-(E)-3-{1′-methyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3′-piperidin]-6-yl}-acrylic acid methyl ester (220 mg, 0.70 mmol) in water (8 ml) and dioxane (16 ml) was treated with 1 M NaOH (0.90 ml) as described in Example 30, Step A to give (±)-(E)-3-{1′-methyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3′-piperidin]-6-yl}-acrylic acid (208 mg) as a yellow solid.

Sources & evidence

ORD record
ord-4641bb20317a421c92819a57ec630b7c
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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