6-Acetylamino-3-methoxy-5,6,7,8-tetrahydronaphthalene-2-sulfonyl chloride → N-(6-mercapto-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide

HRID 2104263Notes

Reaction equation

[C:1]([NH:4][CH:5]1[CH2:14][CH2:13][C:12]2[CH:11]=[C:10]([S:15](Cl)(=O)=O)[C:9]([O:19][CH3:20])=[CH:8][C:7]=2[CH2:6]1)(=[O:3])[CH3:2]>CC#N.CC#N.ClCCCl.[Zn]>[SH:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][C:9]=1[O:19][CH3:20])[CH2:6][CH:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:14][CH2:13]2.[C:1]([NH:4][CH:5]1[CH2:14][CH2:13][C:12]2[CH:11]=[C:10]([S:15][S:15][C:10]3[CH:11]=[C:12]4[C:7](=[CH:8][C:9]=3[O:19][CH3:20])[CH2:6][CH:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:14][CH2:13]4)[C:9]([O:19][CH3:20])=[CH:8][C:7]=2[CH2:6]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 81 °C

Procedure

To a suspension of zinc dust (1.16 g; 17.7 mmol) and dimethylsilyl dichloride (2.4 mL; 17.7 mmol) in MeCN (40 mL) was added a solution of 6-acetylamino-3-methoxy-5,6,7,8-tetrahydronaphthalene-2-sulfonyl chloride (1.13 g; 3.55 mmol) in MeCN/DCE (40/10 mL), at room temperature. The reaction suspension was then heated at 81° C. for 4 h, cooled to room temperature, filtered and the solvent evaporated under reduced pressure. The crude residue was purified by reverse-phase semi-prep HPLC eluting with a MeCN—H2O gradient to yield N-(6-mercapto-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide as a white solid and N-[6-(6-acetylamino-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yldisulfanyl)-7-methoxy-1,2,3,4,-tetrahydronaphthalen-2-yl]acetamide as a tan solid.

Workup

customat room temperature
temperaturecooled to room temperature
filtrationfiltered
customthe solvent evaporated under reduced pressure
customThe crude residue was purified by reverse-phase semi-prep HPLC
washeluting with a MeCN—H2O gradient

Sources & evidence

ORD record: ord-0bcc178bb57e4aa18840d1d2d703e6e5
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576238B2

Reaction notes

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