Dicyclohexylcarbodiimide → HCID 58557022, compound

HRID 469493Notes

Reaction equation

HRID 469493 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.[N:19]12[CH2:26][CH2:25][CH:22]([CH2:23][CH2:24]1)[C@@H:21](O)[CH2:20]2.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH:10]([C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)[C:11]([O:13][C@@H:21]2[CH:22]3[CH2:25][CH2:26][N:19]([CH2:24][CH2:23]3)[CH2:20]2)=[O:12])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 54889931HCID 54889931, compound

Product 1

HCID 58557022HCID 58557022, compoundYield 5.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4-methoxyphenylamino)-2-(thiophen-3-yl)acetic acid (I56) (544 mg, 2.01 mmol), (R)-quinuclidin-3-ol (614 mg, 4.83 mmol), DCC (511 mg, 2.47 mmol), and HOBT (380 mg, 2.48 mmol) in dry THF (160 ml) was stirred at room temperature overnight. The solvent was evaporated, and the residue was partitioned between EtOAc and 2M NaHCO3. The organic phase was further washed with 2M NaHCO3 and brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (DCM/MeOH=95/5 to 7/3) to obtain (R)-quinuclidin-3-yl 2-(4-methoxyphenylamino)-2-(thiophen-3-yl)acetate (40 mg, 5% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between EtOAc and 2M NaHCO3
  3. washThe organic phase was further washed with 2M NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by flash chromatography (DCM/MeOH=95/5 to 7/3)

Sources & evidence

ORD record
ord-725f17559b384b4e93c02b6a6d0c9ffe
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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