Sodium Hydroxide → HCID 67288801, compound

HRID 518191Notes

Reaction equation

C[O:2][C:3](=[O:26])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:22](=[CH:23][CH:24]=1)[O:21][C:11]1([CH2:16][CH2:15][N:14]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:25].[OH-].[Na+]>>[CH3:20][S:17]([N:14]1[CH2:13][CH2:12][C:11]2([CH2:10][C:9](=[O:25])[C:8]3[C:22](=[CH:23][CH:24]=[C:6](/[CH:5]=[CH:4]/[C:3]([OH:26])=[O:2])[CH:7]=3)[O:21]2)[CH2:16][CH2:15]1)(=[O:18])=[O:19]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 66932150HCID 66932150, compound

Product 1

HCID 67288801HCID 67288801, compoundYield 96%

Procedure

(E)-3-{1′-Methanesulfonyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (162 mg, 0.42 mmol) was hydrolyzed with NaOH following the procedure described in Example 1, Step A, giving (E)-3-{1′-methanesulfonyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid as a white solid (147 mg, 96%). The resulting product was treated with NH2OTHP according to the procedure described in Example 1, Step B, giving (E)-3-{1′-methanesulfonyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide. Finally, the removal of the THP protecting group following the procedure described in Example 2 Step D, gave the crude product, which was purified by preparative LC-MS giving 35 mg of (E)-3-{1′-methanesulfonyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-N-hydroxy-acrylamide.

Sources & evidence

ORD record: ord-0cf347880e3f404b8394f6867f877c5f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115148B2

Reaction notes

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