1,1'-Carbonyldiimidazole → HCID 86720264, compound

HRID 1754306Notes

Reaction equation

HRID 1754306 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1(C(N2C=CN=C2)=O)C=CN=C1.[N:31]12[CH2:38][CH2:37][CH:34]([CH2:35][CH2:36]1)[C@@H:33](O)[CH2:32]2>CC#N.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([O:12][C@@H:33]1[CH:34]2[CH2:37][CH2:38][N:31]([CH2:36][CH2:35]2)[CH2:32]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 914043-Quinuclidinol, (-)-HCID 11010409(2S)-2-(((tert-butoxy)carbonyl)amino)-2-phenylacetic acid

Product 1

HCID 86720264HCID 86720264, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-(tert-butoxycarbonylamino)-2-phenylacetic acid (2 g, 7.96 mmol) was dissolved in CH3CN (20 ml). Di(1H-imidazol-1-yl)methanone (1.936 g, 11.94 mmol) was added, and the reaction was stirred at RT for 1 hour. (R)-quinuclidin-3-ol (1.518 g, 11.94 mmol) was added, and the reaction was stirred at RT for 3 hours to achieve completion. The solvent was removed under vacuum to give a solid that was dissolved in ethyl acetate (300 ml). The precipitate was filtered, and the organic solution was washed with 60 ml of K2CO3 30%, dried over Na2SO4 and evaporated under vacuum to give a crude, that was crystallized in ethyl acetate to give (S)—((R)-quinuclidin-3-yl) 2-(tert-butoxycarbonylamino)-2-phenylacetate (1.67 g, 5.2 mmol).

Workup

  1. stirringthe reaction was stirred at RT for 3 hours
  2. customThe solvent was removed under vacuum
  3. customto give a solid
  4. filtrationThe precipitate was filtered
  5. washthe organic solution was washed with 60 ml of K2CO3 30%
  6. dry with materialdried over Na2SO4
  7. customevaporated under vacuum
  8. customto give a crude, that
  9. customwas crystallized in ethyl acetate

Sources & evidence

ORD record
ord-8b5b941030c9499aa0c9c3e3506494c6
Source dataset
uspto-grants-2015_10
Patent number
US09169245B2

Reaction notes

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