Hydrochloric Acid → HCID 67071583, compound

HRID 874268Notes

Reaction equation

HRID 874268 reaction equation
C[O:2][C:3](=[O:26])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:22](=[CH:23][CH:24]=1)[O:21][C:11]1([CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:20])[CH3:19])[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:25].Cl>CC(O)=O>[C:18]([N:14]1[CH2:15][CH2:16][CH2:17][C:11]2([CH2:10][C:9](=[O:25])[C:8]3[C:22](=[CH:23][CH:24]=[C:6](/[CH:5]=[CH:4]/[C:3]([OH:26])=[O:2])[CH:7]=3)[O:21]2)[CH2:12][CH2:13]1)(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67071625HCID 67071625, compound

Product 1

HCID 67071583HCID 67071583, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(±)-(E)-3-[1′-Acetyl-4-oxo-spiro(chromane-2,4′-azepane)-6-yl]-acrylic acid methyl ester (500 mg, 1.40 mmol) was hydrolyzed with HCl and AcOH following the procedure described in Example 22, Step A, giving (E)-3-[1′-acetyl-4-oxo-spiro(chromane-2,4′-azepane)-6-yl]-acrylic acid as a white solid (475 mg, 98.9%). The acid was treated with NH2OTHP according to the procedure described in Example 22, Step C, giving (E)-3-[1-acetyl-4-oxo-spiro(chromane-2,4′-azepane)-6-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (416 mg, 69.7%). Finally, removal of THP protecting group following the procedure described in Example 23, Step D gave (±)-(E)-3-[1′-acetyl-4-oxo-spiro(chromane-2,4′-azepane)-6-yl]-N-hydroxy-acrylamide (43 mg).

Sources & evidence

ORD record
ord-1d607fc79d2643c6a8973f2839444971
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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