Sodium Hydroxide → HCID 67071644, compound

HRID 874335Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 67071673HCID 67071673, compound

Product 1

HCID 67071644HCID 67071644, compound

Procedure

(±)-(E)-3-[1′-Cyclopentyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester (260 mg, 0.704 mmol) was treated with 1 M NaOH according to the procedure described in Example 16 STEP B to give (±)-(E)-3-[1′-cyclopentyl-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′-cyclopentyl-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-cyclopentyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-N-hydroxy-acrylamide hydrochloride as pale brown solid (109 mg, 38% over three steps).

Sources & evidence

ORD record: ord-d974557393d44ca0b7b248a1668e2d5d
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980877B2

Reaction notes

Loading…