Hydrochloric Acid → HCID 16124996, compound

HRID 1945411Notes

Reaction equation

HRID 1945411 reaction equation
[Cl-].[NH4+:2].C[Al](C)C.CO[C:9](=[O:38])[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([NH:17][C:18](=[O:37])[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]34[CH2:36][CH:31]5[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]5)[CH2:28]3)[CH2:34]4)=[CH:23][CH:22]=2)[CH:11]=1.Cl>C1(C)C=CC=CC=1>[C:27]12([C:24]3[CH:25]=[CH:26][C:21]([O:20][CH2:19][C:18]([NH:17][C:12]4[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=4[OH:16])[C:9]([NH2:2])=[O:38])=[O:37])=[CH:22][CH:23]=3)[CH2:28][CH:29]3[CH2:35][CH:33]([CH2:32][CH:31]([CH2:30]3)[CH2:36]1)[CH2:34]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 16124726HCID 16124726, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 16124996HCID 16124996, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

Ammonium chloride (6.5 mg, 0.12 mmol) in anhydrous toluene 2 ml was treated with trimethyl aluminium (in 2.0 M Hexane, 0.26 ml, 0.51 mmol) under nitrogen. After 0.25 h, It was added 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-4-hydroxy-benzoic acid methyl ester (50.1 mg, 0.12 mmol) in toluene 4 ml. The mixture was stirred for 3 h at 80° C. After cooling, the reaction mixture was treated with diluted HCl until no foaming more. The reaction mixture was separated with ethyl acetate and sodium bicarbonate. The organic phase was washed by brine, dried (MgSO4 anh), and concentrated. The residue was purified by preparative TLC(CH2Cl2:MeOH=15:1) to give 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-4-hydroxy-benzamide as a white-solid (12.9 mg, 25.6%-yield).

Workup

  1. temperatureAfter cooling
  2. customThe reaction mixture was separated with ethyl acetate and sodium bicarbonate
  3. washThe organic phase was washed by brine
  4. dry with materialdried (MgSO4 anh)
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC(CH2Cl2:MeOH=15:1)
  7. customto give

Sources & evidence

ORD record
ord-eecb44bba1584d409ed2d8d23a2b3e85
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

Loading…