Dicyclohexylcarbodiimide → HCID 59401082, compound

HRID 77063Notes

Reaction equation

HRID 77063 reaction equation
Cl.[CH3:2][C:3]1[S:7][C:6]([CH:8]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.[N:19]12[CH2:26][CH2:25][CH:22]([CH2:23][CH2:24]1)[C@@H:21](O)[CH2:20]2.N1(O)C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[N:19]12[CH2:26][CH2:25][CH:22]([CH2:23][CH2:24]1)[C@@H:21]([O:10][C:9](=[O:11])[CH:8]([C:6]1[S:7][C:3]([CH3:2])=[CH:4][CH:5]=1)[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:20]2

Participants

6

Reactant 4

HCID 10868Dicyclohexylcarbodiimide2×HCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 67425631(5-Methyl-thiophen-2-yl)-phenylamino-acetic acid hydrochloride

Product 1

HCID 59401082HCID 59401082, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-methyl-thiophen-2-yl)-phenylamino-acetic acid hydrochloride (I268) (220 mg, 0.77 mmol), (R)-quinuclidin-3-ol (338 mg, 2.66 mmol) and 1H-benzo[d][1,2,3]triazol-1-ol (180 mg, 1.33 mmol) in dry THF (15 mL), is added PS-DCC (1.0 g, 1.330 mmol) and the mixture is shaken at RT for 15 hours. Then (R)-quinuclidin-3-01 (49.3 mg, 0.39 mmol) and PS-DCC (291 mg, 0.39 mmol) are added again and the reaction is shaken at RT for other 3 hours. The resin is filtered off and washed several time with EtOAc. The solvent is concentrated and washed with aq. NaHCO3, water and brine. The organic phase is dried over Na2SO4 and evaporated to obtain the title compound as a brown oil (175 mg, 63% yield).

Workup

  1. stirringthe reaction is shaken at RT for other 3 hours
  2. filtrationThe resin is filtered off
  3. washwashed several time with EtOAc
  4. concentrationThe solvent is concentrated
  5. washwashed with aq. NaHCO3, water and brine
  6. dry with materialThe organic phase is dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-025b3f54b1bc4e5288488d13881d3bf4
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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