Dicyclohexylcarbodiimide → HCID 46840576, compound

HRID 76988Notes

Reaction equation

HRID 76988 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.Cl.[C:17]([NH:20][C:21]1[CH:22]=[C:23]([NH:27][CH:28]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:29]([OH:31])=[O:30])[CH:24]=[CH:25][CH:26]=1)(=[O:19])[CH3:18].C1C=CC2N(O)N=NC=2C=1.[N:48]12[CH2:55][CH2:54][CH:51]([CH2:52][CH2:53]1)[C@@H:50](O)[CH2:49]2>C1COCC1>[N:48]12[CH2:55][CH2:54][CH:51]([CH2:52][CH2:53]1)[C@@H:50]([O:30][C:29](=[O:31])[CH:28]([NH:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([NH:20][C:17](=[O:19])[CH3:18])[CH:22]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:49]2

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 67425010(3-Acetylamino-phenylamino)-phenyl-acetic acid hydrochloride

Product 1

HCID 46840576HCID 46840576, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

PS-DCC (798 mg, 0.10 mmol, loading: 1.25 mmol/g) is suspended in dry THF (10 mL). (3-Acetylamino-phenylamino)-phenyl-acetic acid hydrochloride (I45) (160 mg, 0.50 mmol), HOBT (153 mg, 0.10 mmol), and (R)-quinuclidin-3-ol (190 mg, 1.50 mmol) are added and the mixture is shaken for 16 hours at RT (Conversion complete by UPLC/MS-UV). PS-DCC is filtered off and washed with THF and then with EtOAc. The filtrate is evaporated, the resulting residue is taken up with EtOAc and washed with 5% NaHCO3, water and brine. The organic layer is separated, dried over Na2SO4, filtered and evaporated to afford the title compound as a yellow oil (196 mg, quantitative yield, mixture of diastereoisomers).

Workup

  1. filtrationPS-DCC is filtered off
  2. washwashed with THF
  3. customThe filtrate is evaporated
  4. washwashed with 5% NaHCO3, water and brine
  5. customThe organic layer is separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-7122f4f186f04ebaa6fad005b66ec2d7
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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