Sodium Hydroxide → (E)-3-{1'-(2-phenyl-thiazol-4-yl-methyl)-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid

https://huagongshe.com/reaction/2046767

Participants

Role	Name	HCID	Charge
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	(E)-3-{1'-(2-phenyl-thiazol-4-yl-methyl)-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester	HCID 66932473	—
Product	(E)-3-{1'-(2-phenyl-thiazol-4-yl-methyl)-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid	HCID 66932589	95%

Reaction Steps

(E)-3-{1′-(2-phenyl-thiazol-4-yl-methyl)-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (600 mg, 1.26 mmol) was treated with 1 M NaOH following the procedure described in Example 71 Step B, giving (E)-3-{1′-(2-phenyl-thiazol-4-yl-methyl)-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid (548 mg, 95%). The resulting product was treated with NH2OTHP according to the procedure described in Example 71 Step C, giving (E)-3-{1′-(2-phenyl-thiazol-4-yl-methyl)-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide. Finally, removal of the THP protecting group following the procedure described in Example 71 Step C gave (E)-3-{1′-(2-phenyl-thiazol-4-yl-methyl)-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-N-hydroxy-acrylamide hydrochloride (202 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08592444B2
Source dataset	uspto-grants-2013_11
ORD ID	ord-4a91421121a446ed9d07a10a3228756e
Source note	uspto-grants-2013_11