Hydrochloric Acid → HCID 19359181, compound

HRID 1417895Notes

Reaction equation

HRID 1417895 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]([I:12])=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].Cl.C(N(CC)CC)C.[CH3:21][C:22]([O:25][C:26](ON=C(C1C=CC=CC=1)C#N)=[O:27])([CH3:24])[CH3:23]>O.O1CCCC1>[C:22]([O:25][C:26]([C:4]1[C:3]([CH2:2][NH2:1])=[CH:11][CH:10]=[C:9]([I:12])[C:5]=1[C:6]([OH:8])=[O:7])=[O:27])([CH3:24])([CH3:23])[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 17791945HCID 17791945, compound

Product 1

HCID 19359181HCID 19359181, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 3-aminomethyl-6-iodobenzoic acid.HCl (8.0 g, 26 mmol) and triethylamine (8.7 g, 86 mmol) in 32 ml of H2O, was added to a solution of Boc-ON (8.0 g, 32 mmol) in 23 ml of tetrahydrofuran cooled to 0° C. The reaction mixture was stirred at room temperature for overnight, and the volatile compounds were removed by concentration under reduced pressure. The residue was diluted with H2O, washed with ether, acidified to pH 3 with 1N HCl, and extracted with ethyl acetate. The extracts were washed with H2O, brine, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure. This material was triturated from ether to provide the title compound (5.7 g, 59%) as a white powder; mp 182° C. (dec); 1H NMR (D6-DMSO) 13.35 (br s, 1H), 7.95 (d, 1H), 7.60 (s, 1H), 7.50 (br t, 1H), 7.10 (d, 1H), 4.10 (d, 2H), 1.40 (s, 9H).

Workup

  1. customthe volatile compounds were removed by concentration under reduced pressure
  2. additionThe residue was diluted with H2O
  3. washwashed with ether
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with H2O, brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated to dryness under reduced pressure
  8. customThis material was triturated from ether

Sources & evidence

ORD record
ord-f6eebc91603e4f78a4889ab4d94fe4d3
Source dataset
uspto-grants-1999_03
Patent number
US05879657

Reaction notes

Loading…