Ethanolamine → HCID 67366053, compound

HRID 81334Notes

Reaction equation

HRID 81334 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]([O:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([OH:31])=O)=[CH:27][CH:26]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[CH2:34]([CH2:36][NH2:37])[OH:35]>C1COCC1>[C:13]([O:17][C:18](=[O:19])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([C:29](=[O:31])[NH:37][CH2:36][CH2:34][OH:35])=[CH:32][CH:33]=1)([CH3:14])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 682631,1'-CarbonyldiimidazoleHCID 67365596HCID 67365596, compound

Product 1

HCID 67366053HCID 67366053, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1′-Carbonyldiimidazole (0.6 g, 3.71 mmol) was added into the solution of 26 (0.91 g, 3.09 mmol) in THF (50 mL). The reaction mixture was stirred at room temperature overnight under argon atmosphere, then ethanolamine (0.28 mL, 4.64 mmol) was added. The stirring was continued for 24 h at room temperature and argon atmosphere. The solvent was evaporated and the residue was purified by Flash™ (BIOTAGE, Inc) (90 g silica gel cartridge 40M, 18:1:0.1 chloroform/ethanol/concentrated ammonium hydroxide). 0.74 g (71%) of a white solid 27 was isolated. 1H NMR (300 MHz, CDCl3) δ 1.40 (s, 9H), 1.48 (m, 2H), 1.60 (m, 2H), 2.62 (m, 2H), 3.10 (m, 2H), 3.79 (m, 2H), 4.55 (br s, 1H), 6.74 (m, 1H), 7.18 (d, 2H), 7.66 (d, 2H).

Workup

  1. waitThe stirring was continued for 24 h at room temperature
  2. customThe solvent was evaporated
  3. customthe residue was purified by Flash™ (BIOTAGE, Inc) (90 g silica gel cartridge 40M, 18:1:0.1 chloroform/ethanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-4d84262d83b649739454472edc5c3f73
Source dataset
uspto-grants-2014_09
Patent number
US08846688B2

Reaction notes

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