4-Chlorobenzoic Acid → HCID 66705951, compound

HRID 2276382Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:29](=[O:30])[C:28]3[CH:32]=[CH:33][C:25]([Cl:24])=[CH:26][CH:27]=3)=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of (S)-4-[2-(4-amino-phenyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (20) in THF (4 ml) were added 4-chlorobenzoic acid (147 mg), N-methylmorpholine (0.27 ml) and TBTU (401 mg). The reaction mixture was heated to 50° C. and stirred for 16 h. The reaction mixture was then concentrated in vacuo and the residue was purified by flash column chromatography (SiO2; gradient: EtOAc/heptane) to afford (S)-4-{2-[4-(4-chloro-benzoylamino)-phenyl]-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester as a white solid (254 mg, 89%). MS (ISP): 478.3 ([{37Cl}M+NH4]+), 476.3 ([{35Cl}M+NH4]+), 405.4 ([{37Cl}M+H—C4H8]+), 403.2 ([{35Cl}M+H—C4H8]+).

Workup

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

Sources & evidence

ORD record: ord-73f1867abe6c42d088511a08ee9c1111
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09132136B2

Reaction notes

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