HCID 9858173, compound → HCID 9879038, compound

HRID 432997Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH2:15][CH2:16][C:17]([CH3:22])([N+:19]([O-])=O)[CH3:18])[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Fe]>[CH3:13][O:12][C:10](=[O:11])[C@H:9]([CH2:14][CH2:15][CH2:16][C:17]([CH3:22])([CH3:18])[NH2:19])[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

Conditions

Temperature: 40 °C

Procedure

Methyl (S)-2-t-butoxycarbonylamino-6-methyl-6-nitroheptanoate (10.05 g, 31.6 mmol) was dissolved in methanol (200 ml). Iron powder (8.81 g, 157.8 mmol) and ferrous sulfate 7 hydrate (40.5 g, 145.6 mmol) were added and the mixture was stirred at 40° C. for 17 h. Since the starting material remained, the insoluble matter was removed by filtration. Iron powder (8.81 g, 157.8 mmol) and ferrous sulfate 7 hydrate (40.5 g, 145.6 mmol) were added and the mixture was stirred at 40° C. for 7 h. The insoluble material was removed by filtration, and methanol was removed by concentration under reduced pressure. Ethyl acetate (300 ml), water (100 ml) and 10% aqueous sodium carbonate solution were added for pH adjustment to 9 and extraction. Ethyl acetate was evaporated by concentration under reduced pressure to give the objective compound (5.01 g, yield 55.0%).

Workup

customthe insoluble matter was removed by filtration
stirringthe mixture was stirred at 40° C. for 7 h
customThe insoluble material was removed by filtration, and methanol
customwas removed by concentration under reduced pressure
additionEthyl acetate (300 ml), water (100 ml) and 10% aqueous sodium carbonate solution were added for pH adjustment to 9 and extraction
customEthyl acetate was evaporated by concentration under reduced pressure

Sources & evidence

ORD record: ord-17f69209b65a4e52a5c6758778d3433b
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06664412B2

Reaction notes

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