Hydrochloric Acid → HCID 15512646, compound

HRID 842768Notes

Reaction equation

HRID 842768 reaction equation
C1O[C:4]2([CH2:9][CH2:8][N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:16]#[N:17])[CH2:6][CH2:5]2)[O:3]C1.Cl>CCOCC.C(=O)(O)[O-].[Na+]>[C:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[N:7]1[CH2:8][CH2:9][C:4](=[O:3])[CH2:5][CH2:6]1)#[N:17]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21273621HCID 21273621, compound

Product 1

HCID 15512646HCID 15512646, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 4 (533 mg, 2.18 mmol) in ether (10 mL) was treated with 5% aqueous HCl (20 mL). The mixture was stirred at room temperature (11 d). The reaction was diluted with ether and neutralized with sodium bicarbonate solution. The aqueous layer was extracted with two additional portions of ether and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 4 mm, 20% EtOAc-80% hexane) afforded the title compound (5).

Workup

  1. extractionThe aqueous layer was extracted with two additional portions of ether
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-69ccabca45d14860815d74218b6d3ef1
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

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