Acetic Acid → HCID 59004666, compound

HRID 1668498Notes

Reaction equation

HRID 1668498 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[CH2:18][CH2:17][C:16](=O)[CH2:15][CH:14]=3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CC(O)=O.Cl.[CH2:25]([NH2:27])C.[OH-].[Na+]>ClCCCl>[CH3:25][NH:27][CH:16]1[CH2:17][CH2:18][C:13]([C:8]2[C:7]3[C:11](=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[NH:10][CH:9]=2)=[CH:14][CH2:15]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 11198Ethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 59004602HCID 59004602, compound

Product 1

HCID 59004666HCID 59004666, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of compound 119 (0.5 g, 1.951 mmol) in 1,2-dichloroethane (10 mL) was treated with AcOH (0.11 mL, 1.951 mmol), ethylamine hydrochloride (0.159 g, 1.951 mmol), NaBH(OAC)3 (0.62 g, 2.926 mmol) at room temperature and stirred for over night (16 h). The reaction was basified with 2N NaOH (25 mL) and product was extracted into ethyl acetate (2×25 mL). The combined ethyl acetate layer washed with brine (15 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 1:9) to obtain compound 126 (0.55 g, 99%) as a semi-solid. 1H NMR (DMSO-d6) δ 1.07 (t, 3H, J=7.2 Hz), 1.47-1.58 (m, 1H), 1.99-2.08 (m, 2H), 2.42-2.59 (m, 3H), 2.67-2.73 (m, 2H), 2.82-2.90 (m, 1H), 6.14 (brs, 1H), 7.81 (s, 1H), 7.86-7.97 (m, 2H), 8.31 (d, 1H, J=2.1 Hz); ESI-MS (m/z, %): 286 (MH+, 100), 241 (33).

Workup

  1. extractionwas extracted into ethyl acetate (2×25 mL)
  2. washThe combined ethyl acetate layer washed with brine (15 mL)
  3. dry with materialdried (Na2SO4)
  4. customSolvent was evaporated
  5. customcrude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 1:9)

Sources & evidence

ORD record
ord-07df8a5a572f40b9af86b3a21f81307e
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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