Tetrahydrofuran → HCID 12046027, compound

HRID 1612376Notes

Reaction equation

C(N(CC)CC)C.[C:8]1([S:18]([NH:21][C@@H:22]([CH2:28][NH2:29])[C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:20])=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1.[Cl:30][C:31]1[C:36]([N+:37]([O-:39])=[O:38])=[C:35](Cl)[N:34]=[CH:33][N:32]=1.C1COCC1>CC(=O)OCC>[Cl:30][C:31]1[N:32]=[CH:33][N:34]=[C:35]([NH:29][CH2:28][C@H:22]([NH:21][S:18]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)(=[O:20])=[O:19])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:36]=1[N+:37]([O-:39])=[O:38]

Participants

Conditions

Temperature: -5 °C

Procedure

2.96 g (29.3 mmol) of triethylamine were added dropwise at −10° C. in the course of 5 minutes to 5.0 g (13.9 mmol) of ethyl (2S)-2-(naphthalene-1-sulfonylamino)-3-aminopropionate (EP 1070707 (EP 99114372.8)) and 2.84 g (14.6 mmol) of 4,6-dichloro-5-nitropyrimidine, dissolved in 140 ml of abs. THF. The mixture was stirred at −5° C. for 15 minutes and then at room temperature for 12 h. The reaction mixture was taken up in EA and extracted with a saturated aqueous NaCl solution, the organic phase was dried over MgSO4 and filtered, and the solvent was distilled off in vacuo. For purification, the residue was chromatographed over silica gel (EA/heptane 3:7). Yield: 6.38 g.

Workup

dissolutiondissolved in 140 ml of abs
waitat room temperature for 12 h
extractionextracted with a saturated aqueous NaCl solution
dry with materialthe organic phase was dried over MgSO4
filtrationfiltered
distillationthe solvent was distilled off in vacuo
customFor purification
customthe residue was chromatographed over silica gel (EA/heptane 3:7)

Sources & evidence

ORD record: ord-95e93ba14f1e4340a9eefefa95553e23
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06992187B2

Reaction notes

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