Methanol → HCID 57563138, compound

HRID 1726291Notes

Reaction equation

CS[C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:31][C:32]2[CH:36]=[CH:35][S:34][CH:33]=2)[CH:10]2[CH2:15][CH2:14][N:13]([C@H:16]([CH3:30])[CH2:17][CH2:18][NH:19][C:20]([C:22]3[C:23]([CH3:29])=[N:24][CH:25]=[N:26][C:27]=3[CH3:28])=[O:21])[CH2:12][CH2:11]2)=[CH:5][CH:4]=1.O[O:38][S:39]([O-:41])=O.[K+].[CH3:43]O>O>[CH3:43][S:39]([C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH2:31][C:32]2[CH:36]=[CH:35][S:34][CH:33]=2)[CH:10]2[CH2:15][CH2:14][N:13]([C@H:16]([CH3:30])[CH2:17][CH2:18][NH:19][C:20]([C:22]3[C:27]([CH3:28])=[N:26][CH:25]=[N:24][C:23]=3[CH3:29])=[O:21])[CH2:12][CH2:11]2)=[CH:7][CH:8]=1)(=[O:41])=[O:38]

Participants

Conditions

Temperature: -15 °C

Procedure

To a solution of COMPOUND 307 (273 mg, 0.522 mmol) in MeOH (5 mL) cooled to −15° C. was added a solution of OXONE® (1.41 g, 2.30 mmol) in H2O (5 mL) and the mixture was stirred at −15° C. for 15 minutes. Standard work-up and purification afforded COMPOUND 308 as a white solid (69 mg, 23%). 1H NMR (CDCl3) δ 0.96-1.25 (m, 2H), 1.03 (d, 3H, J=6.6 Hz), 1.54-1.61 (m, 1H), 1.71-1.84 (m, 3H), 2.21 (t, 1H, J=10.2 Hz), 2.53 (s, 6H), 2.60 (t, 1H, J=11.1 Hz), 2.77-2.92 (m, 3H), 2.99 (s, 3H), 3.31-3.38 (m, 1H), 3.66-3.74 (m, 1H), 3.82-3.89 (m, 1H), 3.98 (s, 2H), 6.67 (d, 2H, J=9.0 Hz), 6.98-7.01 (m, 2H), 7.32 (dd, 1H, J=5.1, 3.0 Hz), 7.66 (d, 2H, J=9.0 Hz), 8.49-8.50 (m, 1H), 8.92 (s, 1H). 13C NMR (CDCl3) δ 13.85, 22.35, 29.53, 30.67, 31.23, 40.34, 43.92, 45.40, 45.54, 52.25, 55.99, 60.54, 112.25, 121.23, 126.45, 126.93, 129.57, 130.66, 131.26, 139.96, 152.59, 157.99, 163.51, 166.72. ES-MS m/z 556 (M+H). Anal. Calcd. for C28H37N5O3S2.0.6H2O: C, 59.36; H, 6.80; N, 12.36; S, 11.32. Found: C, 59.38; H, 6.74; N, 12.07; S, 11.22.

Workup

customStandard work-up and purification

Sources & evidence

ORD record: ord-186ac512b4be45cdbe8d75a826a12fea
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491735B2

Reaction notes

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