Hydrochloric Acid → HCID 69312972, compound

HRID 2054566Notes

Reaction equation

HRID 2054566 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:18][C:19]([OH:21])=O)[CH:15]3[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:17][CH:9]2[CH2:10]4)[CH2:14]3)=[CH:4][CH:3]=1.[Cl-].[NH4+].O.O[N:26]1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.C(N=C=NCCCN(C)C)C.Cl>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:18][C:19]([NH2:26])=[O:21])[CH:15]3[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:17][CH:9]2[CH2:10]4)[CH2:14]3)=[CH:4][CH:3]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 14758532-(4-Chlorophenyl)tricyclo[3.3.1.13,7]decane-2-acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 69312972HCID 69312972, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[2-(4-chlorophenyl)adamantan-2-yl] acetic acid (100 mg, 0.33 mmol) in 4 mL N,N-dimethylformamide (DMF) were added sequentially ammonium chloride (88 mg, 1.6 mmol), 1-hydroxybenzotriazole hydrate (HOBt, 67 mg, 0.49 mmol), N,N-diisopropylethylamine (575 μL, 3.3 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC, 95 mg, 0.49 mmol). The mixture was stirred at room temperature under nitrogen for 2 h, then added to a separatory funnel containing 50 mL of ethyl acetate and aqueous hydrochloric acid (HCl, 1N). The layers were separated and the organic layer was washed sequentially with aqueous N HCl, saturated aqueous sodium bicarbonate, and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo to yield 82 mg of title compound as a white powder which was used without purification.

Workup

  1. additionadded to a separatory funnel
  2. customThe layers were separated
  3. washthe organic layer was washed sequentially with aqueous N HCl, saturated aqueous sodium bicarbonate, and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-304067287b2b4eb9abda62beb723e1bf
Source dataset
uspto-grants-2008_02
Patent number
US07329683B2

Reaction notes

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