Dicyclohexylcarbodiimide → HCID 67605739, compound

HRID 1619571Notes

Reaction equation

HRID 1619571 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:18]12[CH2:25][CH2:24][CH:21]([CH2:22][CH2:23]1)[C@@H:20](O)[CH2:19]2.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[C:10]([O:12][C@@H:20]1[CH:21]2[CH2:24][CH2:25][N:18]([CH2:23][CH2:22]2)[CH2:19]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 15591778BOC-DL-(2)THG-OH

Product 1

HCID 67605739HCID 67605739, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(tert-butoxycarbonylamino)-2-(thiophen-2-yl)acetic acid (710 mg, 2.76 mmol), (R)-quinuclidin-3-ol (421 mg, 3.31 mmol), DCC (683 mg, 3.31 mmol), HOBT (507 mg, 3.31 mmol) in THF (20 ml) was stirred at RT overnight. THF was evaporated, and the crude was portioned between EtOAc and 1M K2CO3. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The crude was purified by flash chromatography (DCM/MeOH=98/2) to obtain (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-(thiophen-2-yl)acetate (509 mg, 50.3% yield).

Workup

  1. customTHF was evaporated
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude was purified by flash chromatography (DCM/MeOH=98/2)

Sources & evidence

ORD record
ord-973f318da70e4ea6bd005fffb8a29906
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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