Triethylamine → HCID 57589077, compound

HRID 1782770Notes

Reaction equation

HRID 1782770 reaction equation
O.ON1C2C=CC=CC=2N=N1.[CH2:12]([O:14][C:15]([C:17]1[CH:18]=[CH:19][C:20]([O:26][CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][O:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:32][CH:31]=2)=[C:21]([CH:25]=1)[C:22](O)=[O:23])=[O:16])[CH3:13].C(N(CC)CC)C.Cl.[NH2:56][C@H:57]1[CH2:62][CH2:61][CH2:60][CH2:59][C@H:58]1[C:63]([O:65][CH2:66][CH3:67])=[O:64]>ClCCl.O>[CH2:66]([O:65][C:63]([C@H:58]1[CH2:59][CH2:60][CH2:61][CH2:62][C@H:57]1[NH:56][C:22]([C:21]1[CH:25]=[C:17]([CH:18]=[CH:19][C:20]=1[O:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][O:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[CH:32][CH:31]=1)[C:15]([O:14][CH2:12][CH3:13])=[O:16])=[O:23])=[O:64])[CH3:67]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2724641ethyl (1R,2S)-2-aminocyclohexane-1-carboxylate hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57589233HCID 57589233, compound

Product 1

HCID 57589077HCID 57589077, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

39 mg (0.20 mmol) of N-[(3-dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (EDC) and 27.4 mg (0.20 mmol) of 1-hydroxy-1H-benzotriazole hydrate (HOBT) are successively added to a suspension of 100 mg (0.20 mmol) of 5-(ethoxycarbonyl)-2-{3-[4-(4-phenoxybutoxy)phenyl]propoxy}benzoic acid in 30 ml of dichloromethane at RT. After 30 min, 41 mg (0.41 mmol) of triethylamine and 38 mg (0.18 mmol) of ethyl cis-2-amino-1-cyclohexanecarboxylate hydrochloride are added, and the mixture is stirred overnight. 10 ml of water are then added, the phases are separated, and the aqueous phase is extracted with dichloromethane (three times 25 ml). The combined organic phases are washed with saturated sodium chloride solution, dried, (sodium sulphate) and concentrated in a rotary evaporator. The crude product is purified by column chromatography (silica gel 60, mobile phase gradient cyclohexane-->cyclohexane-ethyl acetate 5:1). 102 mg of product are obtained.

Workup

  1. customthe phases are separated
  2. extractionthe aqueous phase is extracted with dichloromethane (three times 25 ml)
  3. washThe combined organic phases are washed with saturated sodium chloride solution
  4. customdried
  5. concentration(sodium sulphate) and concentrated in a rotary evaporator
  6. customThe crude product is purified by column chromatography (silica gel 60, mobile phase gradient cyclohexane-->cyclohexane-ethyl acetate 5:1)

Sources & evidence

ORD record
ord-77fa3758660f4895aa3a3902960c4cca
Source dataset
uspto-grants-2009_03
Patent number
US07498460B2

Reaction notes

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