Sodium Hydroxide → HCID 67071687, compound

HRID 874333Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 67071346HCID 67071346, compound

Product 1

HCID 67071687HCID 67071687, compound

Procedure

(±)-(E)-3-[1′-Isopropyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester (234 mg, 0.681 mmol) was treated with 1 M NaOH according to the procedure described in Example 16 STEP B to give (±)-(E)-3-[1′-isopropyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid. The acid was treated with NH2OTHP according to the procedure described in Example 16, Step C, giving (±)-(E)-3-[1′-isopropyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide. Removal of the THP protecting group following the procedure described in Example 16, Step C, gave (±)-(E)-3-[1′-isopropyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-N-hydroxy-acrylamide hydrochloride as yellow powder (210 mg, 81% over three steps)

Sources & evidence

ORD record: ord-ddb8229180904a68a6b01c9143c9003b
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980877B2

Reaction notes

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