4-Methylmorpholine → HCID 13828186, compound

HRID 2221315Notes

Reaction equation

HRID 2221315 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:6](O)=[O:7])[CH:3]([CH3:5])[CH3:4].CN1CCOCC1.[NH:23]1[CH2:31][CH2:30][CH2:29][C@H:24]1[C:25]([O:27][CH3:28])=[O:26].[ClH:32]>C1COCC1>[NH2:1][C@H:2]([C:6]([N:23]1[CH2:31][CH2:30][CH2:29][C@H:24]1[C:25]([O:27][CH3:28])=[O:26])=[O:7])[CH:3]([CH3:5])[CH3:4].[ClH:32]

Participants

5

Reactant 3

HCID 79724-Methylmorpholine2×HCID 83693Boc-L-ValineHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 13828186HCID 13828186, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

Boc-Val-OH (3.00 g, 13.8 mmol) was dissolved in 10 ml of dry THF and cooled down to −15° C. To the mixture CAIBE (1.80 ml, 13.8 mmol) and NMM (1.52 ml, 13.8 mmol) where added and the solution was stirred until the formation of the mixed anhydride was complete. Then the mixture was brought to −10° C. and NMM (1.52 ml, 13.8 mmol) was added followed by H-Pro-OMe.HCl (2.29 g, 13.8 mmol). The mixture was allowed to reach room temperature and left overnight. After removing the solvent and the usual workup the resulting ester 1 was taken without further characterisation. The ester 1 was dissolved in HCl/HOAc (5 ml, 6N) and left at 0° C. until the removal of the Boc-group was complete. The solvent was then removed and the resulting oil was treated with diethylether to give a white solid 2.

Workup

  1. customwas brought to −10° C.
  2. customto reach room temperature
  3. customAfter removing the solvent
  4. dissolutionThe ester 1 was dissolved in HCl/HOAc (5 ml, 6N)
  5. waitleft at 0° C. until the removal of the Boc-group
  6. customThe solvent was then removed
  7. additionthe resulting oil was treated with diethylether

Sources & evidence

ORD record
ord-581463bc495445dbb0155c72b87fe0d1
Source dataset
uspto-grants-2008_05
Patent number
US07368576B2

Reaction notes

Loading…