Triethylamine → HCID 1480126, compound

HRID 466781Notes

Reaction equation

HRID 466781 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C@@H:7]([NH2:10])[CH2:8][OH:9])=[CH:3][CH:2]=1.C(N(CC)CC)C.[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](Cl)=[O:24]>O1CCCC1.CCOCC>[OH:9][CH2:8][C@H:7]([NH:10][C:23]([C:19]1[O:18][CH:22]=[CH:21][CH:20]=1)=[O:24])[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 2724025(R)-beta-aminophenethyl alcohol

Product 1

HCID 1480126HCID 1480126, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of D-(-)-α-phenylglycinol (1.18 g, 8.43 mmole) and triethylamine (3.18 mL, 23 mmole) were dissolved in dry tetrahydrofuran (20 mL), cooled down to 0° C (ice bath) and treated dropwise with furoyl chloride (0.76 mL or 1.0 g, 7.66 mmole). The reaction mixture was stirred at 0° C. for 1.0 hour, diluted with ether (100 mL) and washed with 5% HCl (20 mL). The aqueous phase was re-extracted with ether (100 mL) and the combined ether extracts were washed with brine (20 mL), dried (anhydrous MgSO4), filtered and evaporated to dryness to give the title compound (1.79 g, quantitative crude yield) as a solid, m.p. 130°-131° C.

Workup

  1. washwashed with 5% HCl (20 mL)
  2. extractionThe aqueous phase was re-extracted with ether (100 mL)
  3. washthe combined ether extracts were washed with brine (20 mL)
  4. dry with materialdried (anhydrous MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-e76cead864b54fac9b3cb5bcfa97d02a
Source dataset
uspto-grants-1992_10
Patent number
US05157134

Reaction notes

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