Hydrochloric Acid → HCID 59712405, compound

HRID 2222458Notes

Reaction equation

HRID 2222458 reaction equation
[CH2:1]([O:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][C:9]2([C:14]([O:16]C)=[O:15])[CH2:13][CH2:12][CH2:11][O:10]2)=[CH:6][C:5]=1[CH2:20][OH:21])[CH3:2].N1C=CC=CC=1.[Cl:28][C:29]1[CH:30]=[C:31]([N:35]=[C:36]=[O:37])[CH:32]=[CH:33][CH:34]=1.Cl>O1CCCC1.C(OCC)(=O)C>[Cl:28][C:29]1[CH:30]=[C:31]([NH:35][C:36]([O:21][CH2:20][C:5]2[CH:6]=[C:7]([CH:18]=[CH:19][C:4]=2[O:3][CH2:1][CH3:2])[CH2:8][C:9]2([C:14]([OH:16])=[O:15])[CH2:13][CH2:12][CH2:11][O:10]2)=[O:37])[CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 17968Benzene, 1-chloro-3-isocyanato-HCID 23023483HCID 23023483, compound

Product 1

HCID 59712405HCID 59712405, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.012 g of methyl 2-(4-ethoxy-3-hydroxymethylbenzyl)tetrahydro-2-furancarboxylate in 0.2 ml of tetrahydrofuran were added 0.010 ml of pyridine and 0.0066 g of 3-chlorophenylisocyanic acid, and the mixture was stirred at room temperature for 15 hours. 1 ml of ethyl acetate and 0.5 ml of 1 N hydrochloric acid were added, and the organic layer was concentrated. The residue was dissolved in 0.5 ml of tetrahydrofuran, 0.5 ml of ethanol and 0.2 ml of 1 N sodium hydroxide, and the mixture was stirred for 2 hours. 1 ml of ethyl acetate and 0.5 ml of 1 N hydrochloric acid were added, and the organic layer was concentrated. The residue was purified by HPLC using a reverse-phase column and a water-acetonitrile-trifluoroacetic acid elution solvent system, to give the title compound.

Workup

  1. concentrationthe organic layer was concentrated
  2. dissolutionThe residue was dissolved in 0.5 ml of tetrahydrofuran
  3. stirring0.5 ml of ethanol and 0.2 ml of 1 N sodium hydroxide, and the mixture was stirred for 2 hours
  4. addition1 ml of ethyl acetate and 0.5 ml of 1 N hydrochloric acid were added
  5. concentrationthe organic layer was concentrated
  6. customThe residue was purified by HPLC
  7. washa water-acetonitrile-trifluoroacetic acid elution solvent system

Sources & evidence

ORD record
ord-cfce15e0e94c4bb587f1c7967ed5ba7a
Source dataset
uspto-grants-2008_05
Patent number
US07371777B2

Reaction notes

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