Triethylamine → HCID 67582173, compound

HRID 580884Notes

Reaction equation

HRID 580884 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.C(Cl)(=O)C(Cl)=O.[Cl:26][C:27]1[CH:28]=[C:29]([NH:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH:30]=[CH:31][CH:32]=1>ClCCl.CCOC(C)=O>[C:4]([O:3][C:1]([NH:8][CH2:9][C:10]([N:33]([C:29]1[CH:30]=[CH:31][CH:32]=[C:27]([Cl:26])[CH:28]=1)[CH2:34][C:35]([O:37][CH3:38])=[O:36])=[O:12])=[O:2])([CH3:5])([CH3:6])[CH3:7]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 65578Oxalyl chlorideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 11629788HCID 11629788, compound

Product 1

HCID 67582173HCID 67582173, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Boc-glycine and triethylamine (1.0 equiv.) in dichloromethane at 0° C. is added oxalylchloride (1.0 equiv). After one hour, a solution of the product from Step F (1 equiv.) in dichloromethane is added to the first solution, followed by triethylamine (1 equiv.). The solution is allowed to warm to room temperature. After complete reaction, the solution is poured into EtOAc and washed with sat. NH4Cl soln., sat. NaHCO3 soln., and brine. The solution is dried (Na2SO4), filtered, and concentrated in vacuo. The resulting material is purified by silica gel chromatography to provide the titled compound.

Workup

  1. customAfter complete reaction
  2. washwashed with sat. NH4Cl soln
  3. dry with materialThe solution is dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting material is purified by silica gel chromatography

Sources & evidence

ORD record
ord-8dadbb4b93c4497397c169d9ffcda812
Source dataset
uspto-grants-1999_07
Patent number
US05919785

Reaction notes

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