4-Methylmorpholine → HCID 131721729, compound

HRID 1636333Notes

Reaction equation

HRID 1636333 reaction equation
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([OH:8])=O)[CH:3]([CH3:5])[CH3:4].C[N:17]1CCOCC1.ClC(OCC(C)C)=O.[NH:31](N)[C@H:32]([C:34]([NH:36][C@H:37]([C:42]([N:44]([CH3:47])[O:45][CH3:46])=[O:43])[CH2:38][CH:39]([CH3:41])[CH3:40])=[O:35])[CH3:33].Cl>C1COCC1.O1CCOCC1>[CH3:47][N:44]([C:42](=[O:43])[C@H:37]([CH2:38][CH:39]([CH3:41])[CH3:40])[NH:36][C:34](=[O:35])[C@H:32]([CH3:33])[NH:31][C:6](=[O:8])[C@H:2]([CH:3]([CH3:4])[CH3:5])[N:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[NH2:17])[O:45][CH3:46]

Participants

7

Reactant 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 83693Boc-L-ValineHCID 131721730HCID 131721730, compound

Product 1

HCID 131721729HCID 131721729, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of Boc-Val-OH (46 mmol) and N-methyl morpholine (46 mmol) in THF (20 ml) was added to a pre cooled solution of isobutyl chloroformate (46 mmol) in THF (30 ml) under nitrogen at between -10 and -15° C. over 30 minutes. The reaction was stirred at -10° C. for 1 hour after which time a solution of N-methyl morpholine (46 mmol) and HCl.H2N-Ala-Leu-N(OMe)Me (41.8 mmol) in 1,4-dioxane (30 ml) was added drop wise slowly. The reaction was left for 1 hour at -10° C. and then allowed to warm up to room temperature. After concentrating the solution under high vacuum, water (50 ml) and ethylacetate (200 ml) was added. The organic layer was then washed with 0.1 M citric acid solution (3×50 ml), then saturated sodium bicarbonate (3×50 ml), dried over magnesium sulphate and then concentrated under vacuum to give the product.

Workup

  1. additionwas added drop wise slowly
  2. concentrationAfter concentrating the solution under high vacuum, water (50 ml) and ethylacetate (200 ml)
  3. additionwas added
  4. washThe organic layer was then washed with 0.1 M citric acid solution (3×50 ml)
  5. dry with materialsaturated sodium bicarbonate (3×50 ml), dried over magnesium sulphate
  6. concentrationconcentrated under vacuum
  7. customto give the product

Sources & evidence

ORD record
ord-3bbf9cb4c23840e6b2d1a6397ae08898
Source dataset
uspto-grants-2000_03
Patent number
US06034066

Reaction notes

Loading…