1,2-Dichloroethane → HCID 18512741, compound

HRID 1370740Notes

Reaction equation

[C:1]([NH:4][C@H:5]([C:23]([OH:25])=O)[CH2:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8])(=[O:3])[CH3:2].[O:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[O:32][NH2:33].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:1]([NH:4][CH:5]([CH2:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(=[O:8])=[O:9])[C:23]([NH:33][O:32][CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31][O:26]1)=[O:25])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the title compound of Example 11c (930 mg, 2.45 mmol) and O-tetrahydro-2H-pyran-2-yl-hydroxylamine (287 mg, 2.45 mmol) in anhydrous DMF (40 mL), cooled to zero degrees C., were added EDC (493 mg, 2.57 mmol) and HOBT (393 mg, 2.57 mmol). After stirring at zero degrees C. for 1 hour and at room temperature for 3 hours, the solution was partitioned between EtOAc and H2O. The resulting organic phase was 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 (400 mg, 34%).

Workup

waitat room temperature for 3 hours
customthe solution was partitioned between EtOAc and H2O
washThe resulting organic phase was washed 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-d2204e2a29af40948397bd752f1e9783
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06583299B1

Reaction notes

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