1,2-Dichloroethane → HCID 67605892, compound

HRID 1619573Notes

Reaction equation

HRID 1619573 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:23]12[CH2:30][CH2:29][CH:26]([CH2:27][CH2:28]1)[C@@H:25](O)[CH2:24]2.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[C:10]([O:12][C@@H:25]1[CH:26]2[CH2:29][CH2:30][N:23]([CH2:28][CH2:27]2)[CH2:24]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 333429Stk367969

Product 1

HCID 67605892HCID 67605892, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(tert-butoxycarbonylamino)-3-(1H-indol-3-yl)propanoic acid (100 mg, 0.33 mmol), (R)-quinuclidin-3-ol (50.1 mg, 0.39 mmol), HOBT (53.3 mg, 0.39 mmol) and EDC (76 mg, 0.39 mmol) in DMF (2 ml) was heated at 90° C. for 1.5 hours under microwave irradiation. The solvent was evaporated. The residue was taken up with EtOAc and washed with 1N Na2CO3, water and brine. The organic phase was dried over Na2SO4, filtered and evaporated to obtain (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-3-(1H-indol-3-yl)propanoate (95 mg, 69.9% yield), which was used as such in the next step.

Workup

  1. customThe solvent was evaporated
  2. washwashed with 1N Na2CO3, water and brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-acd8261b83e647f2aebceb92667644a0
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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