Sodium Hydroxide → HCID 86712830, compound

HRID 518235Notes

Reaction equation

C[O:2][C:3](=[O:30])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:26](=[CH:27][CH:28]=1)[O:25][C:11]1([CH2:16][CH2:15][N:14]([CH:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:18])[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:29].[OH-].[Na+]>>[C:19]1([CH:17]([N:14]2[CH2:15][CH2:16][C:11]3([CH2:10][C:9](=[O:29])[C:8]4[C:26](=[CH:27][CH:28]=[C:6](/[CH:5]=[CH:4]/[C:3]([OH:30])=[O:2])[CH:7]=4)[O:25]3)[CH2:12][CH2:13]2)[CH3:18])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 66932587HCID 66932587, compound

Product 1

HCID 86712830HCID 86712830, compoundYield 88%

Procedure

(±)-(E)-3-{1′-(1-Phenyl-ethyl)-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (526 mg, 1.30 mmol) was treated with 1 M NaOH following the procedure described in Example 71 Step B, giving (±)-(E)-3-{1′-(1-phenyl-ethyl)-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid (445 mg, 88%). The resulting product was treated with NH2OTHP according to the procedure described in Example 71 Step C, giving (±)-(E)-3-{1′-(1-phenyl-ethyl)-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′-(1-phenyl-ethyl)-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-N-hydroxy-acrylamide hydrochloride (197 mg).

Sources & evidence

ORD record: ord-9ee6a23f957f49dcbfe1f6de120e51e5
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115148B2

Reaction notes

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