Hydrochloric Acid → HCID 67071618, compound

HRID 874246Notes

Reaction equation

HRID 874246 reaction equation
C[O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:25](=[CH:26][CH:27]=1)[O:24][C:11]1([CH2:15][N:14]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:28].Cl>CC(O)=O>[C:18]1([CH2:17][CH2:16][N:14]2[CH2:15][C:11]3([CH2:10][C:9](=[O:28])[C:8]4[C:25](=[CH:26][CH:27]=[C:6](/[CH:5]=[CH:4]/[C:3]([OH:29])=[O:2])[CH:7]=4)[O:24]3)[CH2:12][CH2:13]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67071414HCID 67071414, compound

Product 1

HCID 67071618HCID 67071618, compoundYield 107.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(±)-(E)-3-[1′-(2-Phenyl-ethyl)-4-oxo-spiro[chromane-2,4′-pyrrolidine]-6-yl]-acrylic acid methyl ester (280 mg, 0.71 mmol) was hydrolyzed with HCl and AcOH following the procedure described in Example 1, Step A, giving (±)-(E)-3-[1′-(2-phenyl-ethyl)-4-oxo-spiro[chromane-2,4′-pyrrolidine]-6-yl]-acrylic acid as a white solid (288 mg, 98%). The acid was treated with NH2OTHP according to the procedure described in Example 1, Step C, giving (E)-3-[1′-(2-phenyl-ethyl)-4-oxo-spiro[chromane-2,4′-pyrrolidine]-6-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide as a yellow solid (103 mg, 0.22 mmol, 31%). Finally, removal of THP protecting group following the procedure described in Example 1, Step D gave (±)-(E)-3-[1′-(2-phenyl-ethyl)-4-oxo-spiro[chromane-2,4′-pyrrolidine]-6-yl]-N-hydroxy-acrylamide hydrochloride (33.7 mg, 36%) as a white solid.

Sources & evidence

ORD record
ord-eab22201a2834598b69934958c80dd18
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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