4-Methylmorpholine → HCID 14796012, compound

HRID 1587590Notes

Reaction equation

HRID 1587590 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].CN1CCOCC1.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)=[O:24]>C(Cl)Cl>[N+:32]([C:29]1[CH:30]=[CH:31][C:26]([O:25][C:23]([NH:6][C@H:5]([C:4]([O:3][CH3:2])=[O:14])[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:24])=[CH:27][CH:28]=1)([O-:34])=[O:33]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 14796012HCID 14796012, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

To a suspension of phenylalanine methyl ester hydrochloride (2.15 g, 10.0 mmols) in methylene chloride (40 mL) at -30° C. was added N-methylmorpholine (2.2 mL, 20 mmols) followed by p-nitrophenyl chloroformate (2.01 g, 10 mmols). The resulting mixture was stirred at -30° C. for 15 minutes, then for 15 minutes at 25° C., after which it was washed sequentially with 1N hydrochloric acid and saturated aqueous sodium bicarbonate solution, dried, and concentrated. The residue (2.96 g) was crystallized from acetonitrile to give the title A compound (1.22 g), m.p. 130°-131° C., [α]D +88° (c=1.5, CHCl3). The mother liquor was chromatographed on silica gel (90 g), eluting with benzene:ethyl acetate (9:1) to give an additional 760 mg of the title A compound (total yield 1.98 g).

Workup

  1. waitfor 15 minutes at 25° C.
  2. washafter which it was washed sequentially with 1N hydrochloric acid and saturated aqueous sodium bicarbonate solution
  3. customdried
  4. concentrationconcentrated
  5. customThe residue (2.96 g) was crystallized from acetonitrile

Sources & evidence

ORD record
ord-5e52afbb517c4b1cbdbe37e76e9cb5c3
Source dataset
uspto-grants-1993_06
Patent number
US05217958

Reaction notes

Loading…