4-Methylmorpholine → HCID 7216907, compound

HRID 1457825Notes

Reaction equation

HRID 1457825 reaction equation
[NH:1]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:2]([C:12]([OH:14])=O)[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C[N:23]1CCO[CH2:25][CH2:24]1.C(OC(Cl)=O)C(C)C>C1COCC1>[NH:1]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:2]([C:12]([NH:23][CH2:24][CH3:25])=[O:14])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-

Product 1

HCID 7216907HCID 7216907, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Boc-Ser(Bzl), (6.0 gm, 20.3 mmol) and N-methylmorpholine, 2.3 mL, (20.9 mmol) in 50 mL of THF, was added isobutylchloroformate (2.7 mL, 20.8 mmol), at -15° C. The solution was stirred for a few minutes, and gaseous ethylamine was bubbled through the mixture. The mixture was allowed to stir at -15° C. for 30 min. It was then filtered and the filtrate was concentrated to dryness. The resulting residue was dissolved in ethyl acetate (100 mL), and was washed successively with 1M HCl (2×50 mL), water (50 mL), 10% Na2 CO3 (2×50 mL), and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to yield 6.0 gm of a white powder. The structure was supported by NMR data.

Workup

  1. customat -15° C
  2. customgaseous ethylamine was bubbled through the mixture
  3. stirringto stir at -15° C. for 30 min
  4. filtrationIt was then filtered
  5. concentrationthe filtrate was concentrated to dryness
  6. dissolutionThe resulting residue was dissolved in ethyl acetate (100 mL)
  7. washwas washed successively with 1M HCl (2×50 mL), water (50 mL), 10% Na2 CO3 (2×50 mL), and brine (50 mL)
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-b93564d451b94a23911704a48b23dcfa
Source dataset
uspto-grants-1998_12
Patent number
US05849690

Reaction notes

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