Ethanolamine → HCID 59737532, compound

HRID 1907721Notes

Reaction equation

HRID 1907721 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]2[CH:9]=[CH:10][C:11]([N+:25]([O-:27])=[O:26])=[C:12]([NH:14][C:15](=[O:24])[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH:13]=2)=[CH:5][CH:4]=1)=O.[CH2:28]([CH2:30][NH2:31])[OH:29].C([O-])([O-])=O.[K+].[K+].C(O)(C)C>ClCCCl.C(Cl)Cl.C(N(CC)CC)C.CO>[OH:29][CH2:28][CH2:30][NH:31][CH2:1][C:3]1[S:7][C:6]([C:8]2[CH:9]=[CH:10][C:11]([N+:25]([O-:27])=[O:26])=[C:12]([NH:14][C:15](=[O:24])[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH:13]=2)=[CH:5][CH:4]=1

Participants

9

Reactant 4

HCID 700EthanolamineHCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 59737228HCID 59737228, compound

Product 1

HCID 59737532HCID 59737532, compoundYield 44.2%

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolvent2×HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

A solution of aldehyde 191 (0.155 g, 0.41 mmol) in 1,2-dichloroethane (3.0 mL) was treated with ethanolamine (0.06 mL, 1 mmol) and the mixture was allowed to stir at room temperature for 6 h. The mixture was then treated with solid NaHB(OAc)3 (0.354 g, 1.67 mmol), more 1,2-dichloroethane (3 mL) and stirred a further 17 h at room temperature. The mixture was treated with 10% aqueous K2CO3, extracted with DCM, dried over MgSO4, filtered and concentrated. The residue was purified by flash column chromatography (eluent: 5 to 10% isopropanol in DCM with 1% triethylamine then 5 to 10% MeOH in DCM with 1% triethylamine, to give title compound 192 (77.5 mg, 44% yield).

Workup

  1. stirringstirred a further 17 h at room temperature
  2. extractionextracted with DCM
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (eluent

Sources & evidence

ORD record
ord-1d4701a9d2a340f4ba2bb607f980ee13
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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