Dicyclohexylcarbodiimide → HCID 67607395, compound

HRID 1619539Notes

Reaction equation

HRID 1619539 reaction equation
[C:1]([O:5][C:6]([NH:8][CH: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].[CH3:19][N:20]1[CH2:24][CH2:23][C@@H:22](O)[CH2:21]1.C(=NC1CCCCC1)=NC1CCCCC1.N1(O)C2C=CC=CC=2N=N1>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([O:12][C@@H:22]1[CH2:23][CH2:24][N:20]([CH3:19])[CH2:21]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 5718052-(((Tert-butoxy)carbonyl)amino)-2-phenylacetic acidHCID 69513321-Methyl-3-pyrrolidinol, (-)-

Product 1

HCID 67607395HCID 67607395, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(tert-butoxycarbonylamino)-2-phenylacetic acid (I3) (400 mg, 1.59 mmol) in THF (20 ml), were added (R)-1-methylpyrrolidin-3-ol (193 mg, 1.91 mmol), N,N′-methanediylidenedicyclohexanamine (394 mg, 1.91 mmol), and 1H-benzo[d][1,2,3]triazol-1-ol (258 mg, 1.91 mmol). The reaction was stirred at RT for 15, hours, and then the solvent was evaporated. The residue was taken up with DCM, the insoluble was filtered off, and the clear solution was washed twice with aq. Na2CO3 and brine, dried over Na2SO4 and evaporated to obtain (R)-1-methylpyrrolidin-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate (340 mg; 64% yield).

Workup

  1. customthe solvent was evaporated
  2. filtrationthe insoluble was filtered off
  3. washthe clear solution was washed twice with aq. Na2CO3 and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-3ee021b2c6e644c98a1cf2ff1176d2fc
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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