Dicyclohexylcarbodiimide → HCID 58556929, compound

HRID 1044039Notes

Reaction equation

HRID 1044039 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.Cl.[CH3:17][NH:18][C:19]([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:20].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>[CH3:17][NH:18][C:19]([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]([O:31][C@@H:50]2[CH:51]3[CH2:54][CH2:55][N:48]([CH2:53][CH2:52]3)[CH2:49]2)=[O:30])[CH:24]=[CH:25][CH:26]=1)=[O:20]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 67124811HCID 67124811, compound

Product 1

HCID 58556929HCID 58556929, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

PS-DCC (798 mg, 0.998 mmol, loading: 1.25 mmol/g) was suspended in dry THF (10 ml). 2-(3-(Methylcarbamoyl)phenylamino)-2-phenylacetic acid hydrochloride (I9) (160 mg, 0.50 mmol), HOBT (153 mg, 0.10 mmol), and (R)-quinuclidin-3-ol (190 mg, 1.50 mmol) were added, and the mixture was shaken at room temperature for 16 hours (UPLC-MS: complete conversion). PS-DCC was removed by filtration and washed with THF and EtOAc. The filtrate was evaporated and the resulting residue was dissolved in EtOAc and washed with NaHCO3, water and brine. The organic layer was separated, dried over Na2SO4, filtered and evaporated. The resulting oil (196 mg, quantitative yield, mixture of diastereomers) was used for the next step without any further purification.

Workup

  1. customPS-DCC was removed by filtration
  2. washwashed with THF and EtOAc
  3. customThe filtrate was evaporated
  4. dissolutionthe resulting residue was dissolved in EtOAc
  5. washwashed with NaHCO3, water and brine
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. additionThe resulting oil (196 mg, quantitative yield, mixture of diastereomers)
  11. customwas used for the next step without any further purification

Sources & evidence

ORD record
ord-67d26a4ac234475b9453d8018ca923e6
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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