4-Methylmorpholine → HCID 67151588, compound

HRID 1805257Notes

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)[C@H:11]([CH3:22])[O:10][C:9]1([CH3:24])[CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:25]([O:27][C:28]1[N:29]=[CH:30][C:31]([C:34](O)=[O:35])=[N:32][CH:33]=1)[CH3:26].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:34]([C:31]3[CH:30]=[N:29][C:28]([O:27][CH2:25][CH3:26])=[CH:33][N:32]=3)=[O:35])=[CH:19][CH:20]=2)[C@H:11]([CH3:22])[O:10][C:9]1([CH3:23])[CH3:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of (4S,5S)-4-[2-(4-amino-phenyl)-ethyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (120 mg) and 5-ethoxypyrazine-2-carboxylic acid (72.4 mg) in THF (3 ml) were added N-methylmorpholine (158 μl) and TBTU (230 mg). The reaction mixture was capped and shaken at 50° C. overnight. The crude reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, gradient: 0% to 70% EtOAc in hexane) to afford (4S,5S)-4-(2-{4-[(5-ethoxy-pyrazine-2-carbonyl)-amino]-phenyl}-ethyl)-2,2,5-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester as a white solid (167 mg, 96%). MS (ISP): 507.3 ([M+Na]+), 502.3 ([M+NH4]+), 485.3 ([M+H]+), 429.3 ([M-C4H8]+).

Workup

customThe reaction mixture was capped
customThe crude reaction mixture
concentrationwas concentrated in vacuo
customthe residue was purified by flash chromatography (silica gel, gradient: 0% to 70% EtOAc in hexane)

Sources & evidence

ORD record: ord-dd4a540497094cb4961db9b088068d6a
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354441B2

Reaction notes

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