Toluene → HCID 69493322, compound

HRID 347420Notes

Reaction equation

HRID 347420 reaction equation
[CH:1]1([NH:7][C:8](=[O:39])[N:9]([CH2:18][CH2:19][O:20][C@@H:21]2[CH2:26][CH2:25][CH2:24][C@H:23]([CH2:27][CH2:28][CH:29]([CH2:37][CH3:38])[C:30]([O:32]C(C)(C)C)=[O:31])[CH2:22]2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>ClCCl>[CH:1]1([NH:7][C:8](=[O:39])[N:9]([CH2:18][CH2:19][O:20][C@@H:21]2[CH2:26][CH2:25][CH2:24][C@H:23]([CH2:27][CH2:28][CH:29]([CH2:37][CH3:38])[C:30]([OH:32])=[O:31])[CH2:22]2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 69493856HCID 69493856, compound

Product 1

HCID 69493322HCID 69493322, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

160 mg of tert-butyl 4-(cis-3-{2-[3-cyclohexyl-1-(4-methylbenzyl)ureido]ethoxy}cyclohexyl)-2-ethylbutyrate are dissolved in 16 ml of dichloromethane, and 4 ml of trifluoroacetic acid are added. The mixture is stirred at room temperature for 12 hours. 50 ml of toluene are then added, and the solvents are removed under reduced pressure. The residue is purified by RP-HPLC. Freeze drying gives 123 mg of 4-(cis-3-{2-[3-cyclohexyl-1-(4-methylbenzyl)ureido]ethoxy}cyclohexyl)-2-ethylbutyric acid as a colorless oil. C29H46N2O4 (486.70), MS(ESI): 487 (M+H+).

Workup

  1. customthe solvents are removed under reduced pressure
  2. customThe residue is purified by RP-HPLC
  3. customFreeze drying

Sources & evidence

ORD record
ord-3a07c5e0648a4b2fbf6b06cc2589aca3
Source dataset
uspto-grants-2007_02
Patent number
US07173151B2

Reaction notes

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