Sodium Hydroxide → HCID 67071528, compound

HRID 874328Notes

Reaction equation

C[O:2][C:3](=[O:33])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]2[O:30][C:13]3([CH2:18]C[CH2:16][N:15]([CH2:19][C:20]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:22]([CH3:29])[CH:21]=4)[CH2:14]3)N[C:11](=[O:31])[C:10]=2[CH:32]=1.[OH-].[Na+]>>[CH3:29][N:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]([CH2:19][N:15]2[CH2:14][C:13]3([CH2:18][C:11](=[O:31])[C:10]4[C:9](=[CH:8][CH:7]=[C:6](/[CH:5]=[CH:4]/[C:3]([OH:2])=[O:33])[CH:32]=4)[O:30]3)[CH2:16]2)=[CH:21]1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 67071719HCID 67071719, compound

Product 1

HCID 67071528HCID 67071528, compoundYield 66.4%

Procedure

(±)-(E)-3-{1′-(1-Methyl-1H-indol-3-ylmethyl)-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3′-piperidin]-6-yl}-acrylic acid methyl ester (250 mg, 0.561 mmol) was hydrolyzed with 1 M NaOH (0.73 ml) following the procedure described in Example 30, Step A, giving (E)-3-[1′-(1-methyl-1H-indol-3-ylmethyl)-4-oxo-spiro(chromane-2,3′-azetidine)-6-yl]-acrylic acid (150 mg) as a brown solid.

Sources & evidence

ORD record: ord-0992ec14d0ac41e180a626ef68e9acdf
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980877B2

Reaction notes

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