Hydrochloric Acid → HCID 19359164, compound

HRID 1417894Notes

Reaction equation

HRID 1417894 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH2:11][NH2:12].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]([CH2:11][NH2:12])=[C:2]([Cl:1])[CH:10]=[CH:9][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 19044177HCID 19044177, compound

Product 1

HCID 19359164HCID 19359164, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 4-chloro-3-aminomethylbenzoic acid.HCl (6.7 g, 30 mmol) and triethylamine (9.3 g, 92 mmol) in 50 ml of H2O, was added to a solution of Boc-ON (9.2 g, 38 mmol) in 50 ml of tetrahydrofuran cooled to 0° C. The reaction mixture was stirred at room temperature 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 with ether-hexane to provide the title compound (7.4 g, 87%) as a white powder. mp 159° C. (dec); 1H NMR (D6 -DMSO) 13.20 (br s, 1H), 7.90 (s, 1H), 7.80 (dd, 1H), 7.60 (br s, 1H), 7.55 (d, 1H), 4.20 (br 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 with ether-hexane

Sources & evidence

ORD record
ord-a031ce9d269c45f3b961ea3b237a8f1c
Source dataset
uspto-grants-1999_03
Patent number
US05879657

Reaction notes

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