Hydrochloric Acid → HCID 67071728, compound

HRID 874249Notes

Reaction equation

HRID 874249 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][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:12]1)[CH2:10][C:9]2=[O:28].Cl>CC(O)=O>[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:13]2[CH2:14][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]2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67071636HCID 67071636, compound

Product 1

HCID 67071728HCID 67071728, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

This ester was hydrolyzed with aqueous 20% HCl solution and AcOH following the procedure described in Example 1, Step A, giving (±)-(E)-3-[1′-(4-fluoro-benzyl)-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid (305 mg, 0.73 mmol, 96%) as a light brown solid (hydrochloride salt). This was treated with NH2OTHP following the procedure described in Example 1, Step C, giving (±)-(E)-3-[1′-benzyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (288 mg, 0.60 mmol, 82%) as a light yellow solid. This was treated with HCl in diethyl ether as described in example 3, Step D, giving (±)-(E)-3-[1′-(4-fluoro-benzyl)-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-N-hydroxy-acrylamide (188 mg, 0.43 mmol, 74%) as a light pink solid (hydrochloride salt).

Sources & evidence

ORD record
ord-920ab2c840e94a5c8c002414d951710e
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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