2-Amino-1-butanol, (-)- → 2-((R)-1-Hydroxymethyl-propylamino)-N-(3-methanesulfonyl-5-nitro-phenyl)-acetamide

HRID 1957981Notes

Reaction equation

Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:7]=1)=[O:4].[NH2:19][C@H:20]([CH2:23][CH3:24])[CH2:21][OH:22]>C(OCC)(=O)C>[OH:22][CH2:21][C@H:20]([NH:19][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:7]=1)=[O:4])[CH2:23][CH3:24]

Participants

Conditions

Temperature: 75 °C

Procedure

2-Chloro-N-(3-methanesulfonyl-5-nitro-phenyl)-acetamide (750 mg; 2.56 mmol) was diluted in 40 of ethyl acetate, (R)-(−)-2-amino-1-butanol (1.01 ml; 10.25 mmol) was added and the reaction mixture was stirred at 75° C. overnight. The solvent was concentrated under vacuum and the crude was purified by flash chromatography (Isolute Silica cartridge 10 g; eluent: Dichloromethane:MeOH=99:1). 380 mg (1.10 mmol; 43% yield) of the desired 2-((R)-1-Hydroxymethyl-propylamino)-N-(3-methanesulfonyl-5-nitro-phenyl)-acetamide were obtained.

Workup

additionwas added
concentrationThe solvent was concentrated under vacuum
customthe crude was purified by flash chromatography (Isolute Silica cartridge 10 g; eluent: Dichloromethane:MeOH=99:1)

Sources & evidence

ORD record: ord-d1e8f5f0aea146c3901a00ddfb1b4694
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410100B2

Reaction notes

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