Sodium Hydroxide → HCID 66932381, compound

HRID 518193Notes

Reaction equation

C[O:2][C:3](=[O:31])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:27](=[CH:28][CH:29]=1)[O:26][C:11]1([CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:30].[OH-].[Na+]>>[C:20]1([CH2:19][CH2:18][CH2:17][N:14]2[CH2:15][CH2:16][C:11]3([CH2:10][C:9](=[O:30])[C:8]4[C:27](=[CH:28][CH:29]=[C:6](/[CH:5]=[CH:4]/[C:3]([OH:31])=[O:2])[CH:7]=4)[O:26]3)[CH2:12][CH2:13]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 66932374HCID 66932374, compound

Product 1

HCID 66932381HCID 66932381, compoundYield 99.2%

Procedure

(E)-3-{1′-(3-Phenyl-propyl)-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (173 mg, 0.41 mmol) was hydrolyzed with NaOH following the procedure described in Example 1, Step A, giving (E)-3-{1′-(3-phenyl-propyl)-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid as a white solid (165 mg, 98%). The resulting product was treated with NH2OTHP according to the procedure described in Example 1, Step B, giving (E)-3-{1′-(3-phenyl-propyl)-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide. Removal of the THP protecting group following the procedure described in Example 2, Step D gave (E)-3-{1′-(3-phenyl-propyl)l-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-N-hydroxy-acrylamide hydrochloride salt as a white solid (48 mg).

Sources & evidence

ORD record: ord-42da104a58c6495785f8b89325c48145
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115148B2

Reaction notes

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