4-Chloroaniline → HCID 67151580, compound

HRID 1805238Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([OH:21])=O)=[CH:15][CH:14]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Cl:53][C:54]1[CH:60]=[CH:59][C:57]([NH2:58])=[CH:56][CH:55]=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:21])[NH:58][C:57]3[CH:59]=[CH:60][C:54]([Cl:53])=[CH:55][CH:56]=3)=[CH:15][CH:14]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred suspension of (RS)-4-(4-carboxy-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (80 mg) in THF (4 ml) were added sequentially N-methylmorpholine (0.11 ml), TBTU (160 mg) and 4-chloro-aniline (48 mg) and the mixture was heated at 50° C. for 18 h. The mixture was then concentrated in vacuo and the residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (RS)-4-[4-(4-chloro-phenylcarbamoyl)-phenyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (110 mg, quant.) as a light yellow solid. MS (ISP): 455.2 ([{37Cl}M+Na]+), 453.2 ([{35Cl}M+Na]+), 433.3 ([{37Cl}M+H]+), 431.4 ([{35Cl}M+H]+), 377.3 ([{37Cl}M+H—C4H8]+), 375.3 ([{35Cl}M+H—C4H8]+).

Workup

concentrationThe mixture was then concentrated in vacuo
customthe residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc)

Sources & evidence

ORD record: ord-d4467afdfde94d089b810674d77c8f37
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354441B2

Reaction notes

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