Sodium Thiosulfate → HCID 67278976, compound

HRID 1693057Notes

Reaction equation

[Cl:1]N1C(=O)CCC1=O.[C:9]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C@H:19]([NH:21][C:22](=[O:24])[CH3:23])[CH3:20])=[CH:15][C:14]=1[O:25][CH3:26])(=[O:11])[CH3:10].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C>[C:9]([O:12][C:13]1[CH:18]=[C:17]([Cl:1])[C:16]([C@H:19]([NH:21][C:22](=[O:24])[CH3:23])[CH3:20])=[CH:15][C:14]=1[O:25][CH3:26])(=[O:11])[CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

N-Chlorosuccinimide (2.28 g, 17.1 mmol) was added to a solution of (R)-4-(1-acetamidoethyl)-2-methoxyphenyl acetate (2.86 g, 11.4 mmol) in DMF (50 mL) and the mixture was stirred for 1 hour at 0° C. and then for 15 hours at room temperature. The reaction mixture was poured onto aqueous 20% sodium thiosulfate solution and extracted with DCM 3 times. The combined organic layer was dried over sodium sulfate, filtered and evaporated. The residue was chromatographed on a column of silica gel, eluting with EtOAc-Hexane (1:1) and then MeOH-DCM (1:10), to give a brown solid. The solid was washed with Et2O and dried in vacuo to give the title compound (2.40 g, 74%) as white solid. 1H NMR (270 MHz, CDCl3) δ ppm 1.51 (3H, d, J=7.2 Hz), 2.00 (3H, s), 2.30 (3H, s), 3.83 (3H, s), 5.20-5.40 (1H, m), 5.91 (1H, m), 6.91 (1H, s), 7.06 (1H, s).

Workup

waitfor 15 hours at room temperature
extractionextracted with DCM 3 times
dry with materialThe combined organic layer was dried over sodium sulfate
filtrationfiltered
customevaporated
customThe residue was chromatographed on a column of silica gel
washeluting with EtOAc-Hexane (1:1)
customMeOH-DCM (1:10), to give a brown solid
washThe solid was washed with Et2O
customdried in vacuo

Sources & evidence

ORD record: ord-bc02dbd6a39c42a9874bf689b805db48
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158650B2

Reaction notes

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