1,2-Dichloroethane → HCID 18512747, compound

HRID 1370738Notes

Reaction equation

[O:1]=[C:2]([NH:7][C@H:8]([C:26]([OH:28])=O)[CH2:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:3][CH2:4][CH2:5][CH3:6].[O:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]1[O:35][NH2:36].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[O:28]=[C:26]([NH:36][O:35][CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][O:29]1)[CH:8]([NH:7][C:2](=[O:1])[CH2:3][CH2:4][CH2:5][CH3:6])[CH2:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the title compound of Example 11e (690 mg, 1.64 mmol) and O-tetrahydro-2H-pyran-2-yl-hydroxylamine (192 mg, 1.64 mmol) in anhydrous THF (40 mL), cooled to zero degrees C., was added EDC (330 mg, 1.72 mmol) and HOBT (264 mg, 1.72 mmol). After stirring at zero degrees C. for 5 hours and at room temperature for 18 hours, the solution was concentrated. The residue was dissolved into EtOAc (50 mL) and washed with 1M KHSO4 (2×50 mL), saturated NaHCO3 (2×50 mL), and brine (1×50 mL) and dried over Na2SO4. Purification by chromatography (1:1 EtOAc/hexane) yielded the title compound as a colorless oil (500 mg, 59%): Anal. Calcd. for C25H32N2O6S2: C, 57.67; H, 6.19; N, 5.38. Found: C, 57.48; H, 6.37; N, 5.11.

Workup

waitat room temperature for 18 hours
concentrationthe solution was concentrated
dissolutionThe residue was dissolved into EtOAc (50 mL)
washwashed with 1M KHSO4 (2×50 mL), saturated NaHCO3 (2×50 mL), and brine (1×50 mL)
dry with materialdried over Na2SO4
customPurification by chromatography (1:1 EtOAc/hexane)

Sources & evidence

ORD record: ord-2df6ebaf9ea341b49709e2691c6ca225
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06583299B1

Reaction notes

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