Acetic Acid → HCID 18727100, compound

HRID 842771Notes

Reaction equation

HRID 842771 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1)([O-:3])=[O:2].[NH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:23]([O:22][C:21](=[O:27])[NH:20][CH2:19][CH2:18][NH:17][CH:13]1[CH2:14][CH2:15][N:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:11][CH2:12]1)([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 187201N-BOC-ethylenediamineHCID 2907754HCID 2907754, compoundHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18727100HCID 18727100, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 8 (945 mg, 4.29 mmol), 1 (695 mg, 4.33 mmol), and acetic acid (1.31 g, 21.8 mmol) in methanol (10 mL) was treated with sodium cyanoborohydride (270 mg, 4.29 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue dissolved in dichloromethane and sodium bicarbonate solution. The aqueous layer was extracted with two additional portions of dichloromethane and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 6 mm, 10% EtOH-90% CHCl3) afforded the title compound (9).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in dichloromethane
  3. extractionThe aqueous layer was extracted with two additional portions of dichloromethane
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e0bb2e2e06d4205bf7d78cf491df436
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

Loading…