Hydrochloric Acid → HCID 51357552, compound

HRID 874280Notes

Reaction equation

HRID 874280 reaction equation
Cl.[CH2:2]([N:9]1[CH2:12][C:11]2([CH2:21][C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[C:17](/[CH:23]=[CH:24]/[C:25]([NH:27][O:28]C4CCCCO4)=[O:26])[CH:18]=3)[O:13]2)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CCOCC.C(Cl)Cl>[CH2:2]([N:9]1[CH2:10][C:11]2([CH2:21][C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[C:17](/[CH:23]=[CH:24]/[C:25]([NH:27][OH:28])=[O:26])[CH:18]=3)[O:13]2)[CH2:12]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86671982HCID 86671982, compound

Product 1

HCID 51357552HCID 51357552, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

1 M HCl in Et2O (5.0 ml) was added dropwise to a solution of (E)-3-[1′-benzyl-4-oxo-spiro(chromane-2,3′-azetidine)-6-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (360 g, 0.80 mmol) in DCM (4 ml). The mixture was stirred at RT overnight. The formed precipitate was filtered off, washed with DCM, dried under vacuum and purified by preparative HPLC to give (E)-3-[1′-benzyl-4-oxo-spiro(chromane-2,3′-azetidine)-6-yl]-N-hydroxy-acrylamide (290 mg, trifluoroacetate salt) as a white solid.

Workup

  1. filtrationThe formed precipitate was filtered off
  2. washwashed with DCM
  3. customdried under vacuum
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-652c9b6da58d4dd388bd9b712ae9ee69
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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