Acetic Acid → HCID 67340348, compound

HRID 1668502Notes

Reaction equation

HRID 1668502 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.[CH2:24]([NH2:27])[CH2:25][CH3:26].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>ClCCCl>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[CH2:18][CH2:17][CH:16]([NH:27][CH2:24][CH2:25][CH3:26])[CH2:15][CH:14]=3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 7852PropylamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 59004602HCID 59004602, compound

Product 1

HCID 67340348HCID 67340348, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of compound 119 (0.75 g, 2.926 mmol) in 1,2-dichloroethane (20 mL) was treated with AcOH (0.16 mL, 2.926 mmol), n-propylamine (0.24 g, 2.926 mmol), NaBH(OAc)3 (0.93 g, 4.390 mmol) at room temperature and stirred for over night (16 h). The reaction was basified with 2 N NaOH (25 mL) and product was extracted into ethyl acetate (3×50 mL). The combined ethyl acetate layer was washed with brine (20 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:9) to obtain compound 133 (0.58 g, 66%) as a brown semi-solid. 1H NMR (DMSO-d6) δ 0.89 (t, 3H, J=7.2 Hz), 1.37-1.51 (m, 4H), 1.91-2.00 (m, 2H), 2.44-2.57 (m, 4H), 2.68-2.76 (m, 1H), 6.14 (s, 1H), 7.80 (s, 1H), 7.86-7.97 (m, 2H), 8.30 (d, 1H, J=2.1 Hz), 11.82 (brs, 1H); ESI-MS (m/z, %) 300 (MH+, 100).

Workup

  1. extractionwas extracted into ethyl acetate (3×50 mL)
  2. washThe combined ethyl acetate layer was washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. customSolvent was evaporated
  5. customcrude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:9)

Sources & evidence

ORD record
ord-c9c62476fab245f9963b236926189429
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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