4-Methylmorpholine → HCID 131723956, compound

HRID 1356728Notes

Reaction equation

HRID 1356728 reaction equation
C[N:2]1CCOCC1.ClC(OCC)=O.[N:14]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])([CH3:34])[C@H:15]([C:31](O)=[O:32])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:19][CH:18]=1>C1COCC1>[N:14]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])([CH3:34])[C@H:15]([C:31]([NH2:2])=[O:32])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 7010604N-[(1,1-Dimethylethoxy)carbonyl]-N-methyl-O-(phenylmethyl)-L-tyrosine

Product 1

HCID 131723956HCID 131723956, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under cooling with ice, NMM (0.463 ml, 4.21 mmol) and ethyl chloroformate (0.403 ml, 4.21 mmol) were added to a solution of Boc-N-Me-Tyr(Bzl)—OH (1.35 g, 3.51 mmol) in THF (35 ml), followed by stirring for 15 min. The reaction mixture was stirred for further 30 min., while bubbling gaseous ammonia therein. The reaction mixture was then left standing at room temperature, diluted with ethyl acetate and washed with water and saturated brine. The organic layer was dried over magnesium sulfate and evaporated to remove the solvent under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:1) to give Boc-N-Me-Tyr(Bzl)—NH2 (1.32 g, 98%).

Workup

  1. stirringThe reaction mixture was stirred for further 30 min.
  2. customwhile bubbling gaseous ammonia
  3. waitThe reaction mixture was then left
  4. customstanding at room temperature
  5. additiondiluted with ethyl acetate
  6. washwashed with water and saturated brine
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. customevaporated
  9. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-16e19331921144cba39759ceebbc3e24
Source dataset
uspto-grants-2003_07
Patent number
US06586630B1

Reaction notes

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