1,2-Dichloroethane → HCID 11949417, compound

HRID 643054Notes

Reaction equation

HRID 643054 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C@@:4]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)([OH:8])[CH2:3]1.[O:18]1[CH:22]=[CH:21][C:20]([C:23](O)=[O:24])=[CH:19]1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[Cl:17][C:13]1[CH:12]=[C:11]([C:10]#[C:9][C@@:4]2([OH:8])[CH2:5][CH2:6][CH2:7][C@@H:2]([NH:1][C:23]([C:20]3[CH:21]=[CH:22][O:18][CH:19]=3)=[O:24])[CH2:3]2)[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 111,2-Dichloroethane2×HCID 8471TriethylamineHCID 102683-Furoic acidHCID 68411262HCID 68411262, compound

Product 1

HCID 11949417HCID 11949417, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(+)-(1R,3R)-3-Amino-1-(3-chloro-phenylethynyl)-cyclohexanol (115 mg, 0.46 mmol) was dissolved in DMF (5 ml) and treated with furan-3-carboxylic acid ((63 mg, 0.55 mmol) and EDC (108 mg, 0.55 mmol). After stirring for 1.5 h at room temperature, Et3N (0.55 mmol) was added and stirring continued for 18 h. A second batch of EDC (108 mg, 0.55 mmol) was added and stirring continued for 6 h. EtOAc was added and the mixture washed with aqueous sodium bicarbonate and brine. Drying of the organic phase with Na2SO4, filtration and evaporation afforded a crude product (263 mg) which was purified by chromatography on silica gel to afford the title compound as a white solid (105 mg, 66%). MS (LC/MS): 344.2 [M+H]; [α]D=+95.6° (c=0.5, MeOH).

Workup

  1. stirringstirring
  2. waitcontinued for 18 h
  3. stirringstirring
  4. waitcontinued for 6 h
  5. washthe mixture washed with aqueous sodium bicarbonate and brine
  6. dry with materialDrying of the organic phase with Na2SO4, filtration and evaporation
  7. customafforded a crude product (263 mg) which
  8. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7f6cb572e602457fbb7486a1445dfe35
Source dataset
uspto-grants-2010_04
Patent number
US07696379B2

Reaction notes

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