Hydrochloric Acid → HCID 51356716, compound

HRID 874254Notes

Reaction equation

HRID 874254 reaction equation
Cl.CCOCC.[CH2:7]([N:14]1[CH2:19][CH2:18][CH2:17][C:16]2([CH2:28][C:27](=[O:29])[C:26]3[C:21](=[CH:22][CH:23]=[C:24](/[CH:30]=[CH:31]/[C:32]([NH:34][O:35]C4CCCCO4)=[O:33])[CH:25]=3)[O:20]2)[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(Cl)Cl>[CH2:7]([N:14]1[CH2:19][CH2:18][CH2:17][C:16]2([CH2:28][C:27](=[O:29])[C:26]3[C:21](=[CH:22][CH:23]=[C:24](/[CH:30]=[CH:31]/[C:32]([NH:34][OH:35])=[O:33])[CH:25]=3)[O:20]2)[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86671980HCID 86671980, compound

Product 1

HCID 51356716HCID 51356716, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 M HCl in Et2O (5 ml, 5 mmol) was added dropwise to a solution of (E)-3-[1′-benzyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (260 mg, 0.55 mmol) in DCM (3 ml). After 1 h a white solid precipitated, which was filtered, washed with DCM, dried under vacuum and purified by preparative HPLC to give 180 mg of (±)-(E)-3-[1′-benzyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-N-hydroxy-acrylamide as its trifluoroacetic salt.

Workup

  1. customAfter 1 h a white solid precipitated
  2. filtrationwhich was filtered
  3. washwashed with DCM
  4. customdried under vacuum
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-a4b2f2a1aa2541bba22db496ad83de1b
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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