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

HRID 874227Notes

Reaction equation

HRID 874227 reaction equation
[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]2[O:26][C:13]3([CH2:18][CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]3)[NH:12][C:11](=[O:27])[C:10]=2[CH:28]=1.Cl.COC(=O)/C=C/C1C=C2C(=CC=1)OC1(CNC1)CC2=O>C(Cl)Cl.O1CCOCC1>[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]2[O:26][C:13]3([CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)[NH:12][C:11](=[O:27])[C:10]=2[CH:28]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 67071396(E)-3-[4-oxo-spiro(chromane-2,3'-azetidine)-6-yl]-acrylic acid methyl esterHCID 67071413(+/-)-(E)-3-{1'-tert-butoxycarbonyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3'-piperidin]-6-yl}-acrylic acid methyl ester

Product 1

HCID 67071418(+/-)-(E)-3-{3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3'-piperidin]-6-yl}-acrylic acid methyl esterYield 94.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

(±)-(E)-3-{1′-Tert-butoxycarbonyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3′-piperidin]-6-yl}-acrylic acid methyl ester (1.90 g, 4.72 mmol) in DCM (33 ml) was treated with 4 M HCl in dioxane (5.90 ml) as described for Intermediate 4, Step C, giving (±)-(E)-3-{3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3′-piperidin]-6-yl}-acrylic acid methyl ester (1.35 g, hydrochloride salt) as a light brown solid.

Sources & evidence

ORD record
ord-73d00993994d4abbbeaaf5b4e50850b9
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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