Dicyclohexylcarbodiimide → (S)-((R)-quinuclidin-3-yl) 2-(tert-butoxycarbonylamino)-3-phenylpropanoate

HRID 1619579Notes

Reaction equation

HRID 1619579 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:45]12[CH2:52][CH2:51][CH:48]([CH2:49][CH2:50]1)[C@@H:47](O)[CH2:46]2>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:10]([O:12][C@@H:47]1[CH:48]2[CH2:51][CH2:52][N:45]([CH2:50][CH2:49]2)[CH2:46]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 914043-Quinuclidinol, (-)-

Product 1

HCID 59401188(S)-((R)-quinuclidin-3-yl) 2-(tert-butoxycarbonylamino)-3-phenylpropanoateYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (500 mg, 1.88 mmol), DCC (467 mg, 2.26 mmol), and HOBT (346 mg, 2.26 mmol) in dry THF (15 ml) was stirred for 30 minutes at RT. Then (R)-quinuclidin-3-ol (288 mg, 2.26 mmol) was added portionwise and the reaction was stirred at RT for 16 hours. The solvent was evaporated, the residue was dissolved in EtOAc, and the insoluble was removed by filtration. The organic phase was washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered and evaporated to obtain (S)—((R)-quinuclidin-3-yl) 2-(tert-butoxycarbonylamino)-3-phenylpropanoate (600 mg, 85% yield).

Workup

  1. stirringthe reaction was stirred at RT for 16 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in EtOAc
  4. customthe insoluble was removed by filtration
  5. washThe organic phase was washed with saturated NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-101c79f189e443f7a1207d37ec71d552
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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