Triethylamine → HCID 59619253, compound

HRID 1367596Notes

Reaction equation

HRID 1367596 reaction equation
CO[C:3]([C@H:5]1[CH2:9][C@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])(=[O:12])=[O:11])[CH2:7][C@@H:6]1[O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)=[O:4].C[Al](C)C.C(N(CC)CC)C.Cl.[NH2:40][C:41]1([C:44]#[N:45])[CH2:43][CH2:42]1>C(Cl)Cl.[Cl-].[Na+].O>[C:44]([C:41]1([NH:40][C:3]([C@H:5]2[CH2:9][C@H:8]([S:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])(=[O:12])=[O:11])[CH2:7][C@@H:6]2[O:20][C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)=[O:4])[CH2:43][CH2:42]1)#[N:45]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 16682925TrimethylaluminumHCID 66918780HCID 66918780, compound

Product 1

HCID 59619253HCID 59619253, compoundYield 14.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (1R,2R,4R) and (1S,2S,4S)-4-(2-chloro-benzenesulfonyl)-2-(4-chloro-phenoxy)-cyclopentanecarboxylic acid methyl ester (30 mg, 0.0699 mmol) in DCM (3 ml) was added trimethylaluminium (175 μl, 2M solution in toluene, 0.349 mmol), triethylamine (29.1 μl, 0.210 mmol) and 1-amino-1-cyclopropane-carbonitrile hydrochloride (21 mg, 0.1757 mmol) and the reaction mixture was stirred at 40° C. overnight. The mixture was then cooled to room temperature, diluted with brine and extracted 3 times with DCM. The combined organic layers were washed with water and brine, dried (Na2SO4) and evaporated. The remaining brown semisolid was purified by silica gel chromatography (DCM/MeOH 100:0-98:2) yielding a yellow solid (5 mg) that was triturated with ether to obtain the title compound (3 mg, 9%) as off-white solid. MS (EI): 477.0 (M+H)+.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. extractionextracted 3 times with DCM
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe remaining brown semisolid was purified by silica gel chromatography (DCM/MeOH 100:0-98:2)

Sources & evidence

ORD record
ord-9b59d7ad9caf4daaa1d6768584972928
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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