Dimethyl Sulfoxide → HCID 86606155, compound

HRID 643226Notes

Reaction equation

CO[C:3]([C:5]1C(=O)[N:9]([C:12]2[C:13](=[O:33])[O:14][C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([N:22]2[C:26](=[O:27])[C:25]([C:28](OC)=O)=[CH:24][C:23]2=O)=[CH:17][CH:16]=3)[C:7](=[O:8])[CH:6]=1)=O.[CH2:34]([SH:36])[CH3:35].C[S:38]([CH3:40])=O>>[CH2:5]([CH:6]1[C:7](=[O:8])[N:9]([C:12]2[C:13](=[O:33])[O:14][C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([N:22]2[C:26](=[O:27])[CH:25]([CH2:24][CH3:23])[CH2:28][C:40]2=[S:38])=[CH:17][CH:16]=3)[C:34](=[S:36])[CH2:35]1)[CH3:3]

Participants

Reactant 3

HCID 679Dimethyl Sulfoxide

HCID 6343Ethanethiol

HCID 86606156HCID 86606156, compound

Product 1

HCID 86606155HCID 86606155, compoundYield 83%

Procedure

The reaction of 54 mg (0.12 mmol) of compound 5 in 3 mL dry DMSO with 27 μL ethanethiol (0.36 mmol) was carried out according to the same protocol used to obtain compound 7, giving compound 8 in 83% yield (58 mg, 0.1 mmol). FTIR (KBr) (cm−1): 3000, 1727, 1622, 600. 1H-NMR (DMSO-d6): δ (ppm) 8.24 (s, 1H), 7.53 (d, J=2.63, 1H), 7.36 (dd, J=9.24 Hz, J=2.67 Hz, 1H), 7.24 (d, J=9.24 Hz, 1H), 4.38 (d, 1H), 4.32 (s, 1H), 4.00 (s, 3H), 3.98 (d, J=5.6 Hz, 3H), 3.92 (d, J=5.4 Hz, 1H), 3.87 (d, J=5.6 Hz, 1H), 2.80 (m, 4H), 1.30 (t, J=7.24 Hz, 6H). 13C-NMR (DMSO-d6): δ (ppm) 175.06, 172.67, 168.06, 158.44, 150.63, 137.28, 128.83, 128.32, 124.22, 119.69, 118.47, 117.21, 50.01, 46.23, 42.16, 39.12, 14.24, 12.02. HRMS expected for C25H24N2O10S2: 576.087238; found: 576.087413.

Sources & evidence

ORD record: ord-25cf0cf9f0554f2785b97f8193c69e22
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700375B2

Reaction notes

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