Acetic Acid → Octanedioic acid adamantan-1-ylamide hydroxyamide

HRID 1515407Notes

Reaction equation

HRID 1515407 reaction equation
Cl.[NH2:2][OH:3].[Na].C[O:6][C:7](=O)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:26])[NH:15][C:16]12[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2.C(O)(=O)C>CO.O.C1C=CC2C(C3C=CC(O)=CC=3)(C3C=CC(O)=CC=3)OC(=O)C=2C=1>[OH:3][NH:2][C:7](=[O:6])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:15][C:16]12[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2)=[O:26]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 443297Hydroxyamine hydrochlorideHCID 5360545Sodium2×HCID 670065037-(Adamantan-1-yl-carbamoyl)-heptanoic acid methyl ester

Product 1

HCID 53325741Octanedioic acid adamantan-1-ylamide hydroxyamideYield 68%

Reagents, catalysts & solvents 3

HCID 4764PhenolphthaleinCatalystHCID 887MethanolSolvent4×HCID 962WaterSolvent

Procedure

To a first solution of hydroxylamine hydrochloride (66 mg, 0.950 mmol) and phenolphthalein (0.5 mg) in methanol (3 mL), was added dropwise a second solution of sodium metal (33 mg, 1.435 mmol) in methanol (3 mL) via additional funnel until a pink endpoint was reached and precipitate appeared. To the reaction mixture was added a solution of 7-(adamantan-1-yl-carbamoyl)-heptanoic acid methyl ester (152 mg, 0.474 mmol) in methanol (4 mL) was added, followed by the remainder of the second solution of sodium metal in methanol. The resulting reaction was allowed to stir for 24 hours, then the reaction mixture was diluted with water (15 mL), followed by glacial acetic acid (0.2 mL) with stirring. The resulting precipitate was suction filtered and rinsed using water, then dried at room temperature under vacuum to provide a crude residue which was purified by recrystallization from dichloromethane/hexane to provide Compound 17 (104 mg, 68% yield). 1H NMR (300 MHz, CD3OD) δ 7.31 (br s, 1H), 2.09 (t, J=7.5 Hz, 2H), 2.08-1.98 (m, 11H), 1.71 (m, 6H), 1.59 (m, 4H), 1.33 (m, 4H). 13C NMR (75 MHz, CD3OD) δ 175.7, 173.1, 52.8, 42.5, 38.0, 37.7, 33.9, 31.1, 30.00, 29.96, 27.2, 26.8.

Workup

  1. additionwas added
  2. customThe resulting reaction
  3. stirringwith stirring
  4. filtrationfiltered
  5. washrinsed
  6. customdried at room temperature under vacuum
  7. customto provide a crude residue which
  8. customwas purified by recrystallization from dichloromethane/hexane

Sources & evidence

ORD record
ord-0195bb606e1f445fbd252eb6d1ac1ebe
Source dataset
uspto-grants-2012_07
Patent number
US08222451B2

Reaction notes

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