Hydrochloric Acid → HCID 67071578, compound

HRID 874242Notes

Reaction equation

HRID 874242 reaction equation
C[O:2][C:3](=[O:24])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:20](=[CH:21][CH:22]=1)[O:19][C:11]1([CH2:15][CH2:14][N:13]([C:16](=[O:18])[CH3:17])[CH2:12]1)[CH2:10][C:9]2=[O:23].Cl>CC(O)=O>[C:16]([N:13]1[CH2:14][CH2:15][C:11]2([CH2:10][C:9](=[O:23])[C:8]3[C:20](=[CH:21][CH:22]=[C:6](/[CH:5]=[CH:4]/[C:3]([OH:24])=[O:2])[CH:7]=3)[O:19]2)[CH2:12]1)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67071432HCID 67071432, compound

Product 1

HCID 67071578HCID 67071578, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(±)-(E)-3-[1′-Acetyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid methyl ester (240 mg, 0.73 mmol) was hydrolyzed with HCl and AcOH following the procedure described in Example 1, Step A, giving (±)-(E)-3-[1′acetyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid as a white solid (135.5 mg, 0.43 mmol, 59%). The acid was treated with NH2OTHP according to the procedure described in Example 1, Step C, giving (E)-3-[1′-acetyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide as a light yellow solid (82 mg, 0.20 mmol, 46%). Finally, removal of THP protecting group following the procedure described in Example 2, Step D gave (±)-(E)-3-[1′-acetyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-N-hydroxy-acrylamide (64.2 mg, 97%) as a red solid.

Sources & evidence

ORD record
ord-b966f242b5f24119b52d7470368d7b7a
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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