Hydrochloric Acid → HCID 67071680, compound

HRID 874244Notes

Reaction equation

HRID 874244 reaction equation
C[O:2][C:3](=[O:22])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:18](=[CH:19][CH:20]=1)[O:17][C:11]1([CH2:15][CH2:14][N:13]([CH3:16])[CH2:12]1)[CH2:10][C:9]2=[O:21].Cl>CC(O)=O>[CH3:16][N:13]1[CH2:14][CH2:15][C:11]2([CH2:10][C:9](=[O:21])[C:8]3[C:18](=[CH:19][CH:20]=[C:6](/[CH:5]=[CH:4]/[C:3]([OH:22])=[O:2])[CH:7]=3)[O:17]2)[CH2:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67071596HCID 67071596, compound

Product 1

HCID 67071680HCID 67071680, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(±)-(E)-3-[1′-Methyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid methyl ester (105 mg, 0.35 mmol) was hydrolyzed with HCl and AcOH following the procedure described in Example 1, Step A, giving (±)-(E)-3-[1′-methyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid (110 mg, 0.34 mmol, 98%) as a white solid (hydrochloride salt). The acid was treated with NH2OTHP according to the procedure described in Example 1, Step C, to give (E)-3-[1′-methyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (90 mg, 0.23 mmol, 68%). Finally, removal of THP protecting group following the procedure described in Example 2, Step D and purification by preparative HPLC gave (±)-(E)-3-[1′-methyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-N-hydroxy acrylamide (30.5 mg, 31%) as its trifluoroacetic salt.

Sources & evidence

ORD record
ord-3fea25f8dd4241d995c76db85895e7e4
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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