Ethyl Acetate → HCID 178430658, compound

HRID 1936587Notes

Reaction equation

HRID 1936587 reaction equation
[NH2:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C([N:15]=[C:16](S)[N:17](C(OCC1C=CC=CC=1)=O)[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])C.[C:39]([O:42][CH2:43][CH3:44])(=[O:41])C>O1CCCC1>[CH2:43]([O:42][C:39]([N:15]=[C:16]([NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[NH:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1)=[O:41])[C:44]1[CH:10]=[CH:11][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14115670HCID 14115670, compoundHCID 178465517HCID 178465517, compound

Product 1

HCID 178430658HCID 178430658, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a pale yellow solution of 500 mg of 7-amino-8-methylquinoline in 20 mL of tetrahydrofuran are added 1.18 g of ethyl N,N-bis(benzyloxy-carbonyl)pseudothiourea and 1.01 g of mercuric acetate and the mixture is stirred at room temperature for 1 hour. The suspension is diluted with ethyl acetate and the organic layer is washed with water followed by brine. The aqueous layers are extracted with ethyl acetate; the combined organic layers are dried over magnesium sulfate, filtered and rotary evaporated. The residue is purified by flash column chromatography on silica gel, eluting with 50% ethyl acetate/hexanes and recrystallization from hexanes/methylene chloride to provide 1.257 g of 7-[N2,N3-bis(benzyloxycarbonyl)guanidino]-8-methylquinoline as a white solid.

Workup

  1. washthe organic layer is washed with water
  2. extractionThe aqueous layers are extracted with ethyl acetate
  3. dry with materialthe combined organic layers are dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe residue is purified by flash column chromatography on silica gel
  6. washeluting with 50% ethyl acetate/hexanes and recrystallization from hexanes/methylene chloride

Sources & evidence

ORD record
ord-099df6f801664df8975b42e3153e23fb
Source dataset
uspto-grants-2002_05
Patent number
US06391878B2

Reaction notes

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