4-Methylmorpholine → (1,1-dimethylethyl) (S)-[1-methyl-2-[(2-methyl-2-propenyl)amino]-2-oxoethyl]carbamate

HRID 326887Notes

Reaction equation

HRID 326887 reaction equation
[CH3:1][C:2]([CH3:13])([O:4][C:5]([NH:7][C@H:8]([C:10]([OH:12])=O)[CH3:9])=[O:6])[CH3:3].Cl.[CH3:15][C:16](=[CH2:19])[CH2:17][NH2:18].O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>O1CCCC1>[CH3:9][C@H:8]([NH:7][C:5](=[O:6])[O:4][C:2]([CH3:1])([CH3:3])[CH3:13])[C:10]([NH:18][CH2:17][C:16]([CH3:19])=[CH2:15])=[O:12]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 85082Tert-butoxycarbonylalanineHCID 27960291-Hydroxybenzotriazole hydrateHCID 119537722-Methylallylamine hydrochloride

Product 1

HCID 53642955(1,1-dimethylethyl) (S)-[1-methyl-2-[(2-methyl-2-propenyl)amino]-2-oxoethyl]carbamateYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) mixture of 18.9 parts of (S)-N-[(1,1-dimethylethoxy)carbonyl]alanine, 10.8 parts of 2-methyl-2-propen-1-amine monohydrochloride, 27.0 parts of 1-hydroxy-1H-benzotriazole hydrate and tetrahydrofuran, there were added 10.1 parts of N-methylmorpholine and, after 20 min, 20.6 parts of N,N-methanetetraylbis[cyclohexanamine] under a nitrogen atmosphere. The whole was kept at 0° C. for 1 hour and at room temperature for 12 hours. The solvent was evaporated and the residue was partitioned between dichloromethane and NaHCO3 (sat.). The organic layer was separated, washed with NaCl (sat.), dried, filtered and evaporated, yielding 24.2 parts (99.9%) of (1,1-dimethylethyl) (S)-[1-methyl-2-[(2-methyl-2-propenyl)amino]-2-oxoethyl]carbamate (interm. 63).

Workup

  1. temperatureTo a cooled
  2. waitThe whole was kept at 0° C. for 1 hour and at room temperature for 12 hours
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between dichloromethane and NaHCO3 (sat.)
  5. customThe organic layer was separated
  6. washwashed with NaCl (sat.)
  7. customdried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-e4fcda4fa9f64151bbfc42e04a2bf5de
Source dataset
uspto-grants-1993_12
Patent number
US05270464

Reaction notes

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