Sodium Hydroxide → HCID 66932583, compound

HRID 518197Notes

Reaction equation

C[O:2][C:3](=[O:33])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:29](=[CH:30][CH:31]=1)[O:28][C:11]1([CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:32].[OH-].[Na+]>>[NH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([CH2:18][CH2:17][N:14]2[CH2:15][CH2:16][C:11]3([CH2:10][C:9](=[O:32])[C:8]4[C:29](=[CH:30][CH:31]=[C:6](/[CH:5]=[CH:4]/[C:3]([OH:33])=[O:2])[CH:7]=4)[O:28]3)[CH2:12][CH2:13]2)=[CH:20]1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 66932497HCID 66932497, compound

Product 1

HCID 66932583HCID 66932583, compoundYield 87.3%

Procedure

(E)-3-{1′-[2-(1H-indol-3-yl)ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (129 mg, 0.29 mmol) was hydrolyzed with 4 M NaOH following the procedure described in Example 40, Step B, giving (E)-3-{1′-[2-(1H-indol-3-yl)ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid (109 mg, 87%). The product was treated with NH2OTHP according to the procedure described in Example 40, Step C, giving (E)-3-{1′-[2-(1H-indol-3-yl)ethyl]-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 40, Step C gave (E)-3-{1′-[2-(1H-indol-3-yl)ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-N-hydroxy-acrylamide, which was purified by preparative LC-MS and obtained as its trifluoroacetate salt (37 mg, white solid).

Sources & evidence

ORD record: ord-973afb0389d840e8a3c7936b1971284a
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115148B2

Reaction notes

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