Hydrochloric Acid → HCID 11227276, compound

HRID 915286Notes

Reaction equation

HRID 915286 reaction equation
[C:1]([N:4]([CH2:25][C@@H:26]1[O:30][C:29](=[O:31])[N:28]([C:32]2[CH:37]=[CH:36][C:35]([CH:38]3[CH2:43][CH2:42][S:41](=[O:45])(=[O:44])[CH2:40][CH2:39]3)=[C:34]([F:46])[CH:33]=2)[CH2:27]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:24])[CH2:11][NH:12][C:13](=[O:23])[CH2:14][NH:15]C(OC(C)(C)C)=O)=[O:6])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1.C1COCC1.[ClH:60]>O1CCOCC1>[ClH:60].[C:1]([N:4]([CH2:25][C@@H:26]1[O:30][C:29](=[O:31])[N:28]([C:32]2[CH:37]=[CH:36][C:35]([CH:38]3[CH2:39][CH2:40][S:41](=[O:44])(=[O:45])[CH2:42][CH2:43]3)=[C:34]([F:46])[CH:33]=2)[CH2:27]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:24])[CH2:11][NH:12][C:13](=[O:23])[CH2:14][NH2:15])=[O:6])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 8028TetrahydrofuranHCID 11445297HCID 11445297, compound

Product 1

HCID 11227276HCID 11227276, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Following general procedure G, (R)-(2-tert-Butoxycarbonylamino-acetylamino)-acetic acid (acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamoyloxy)-methyl ester (12i) (0.48 g, 0.71 mmol), anisole (0.1 mL), THF (14 mL), and 4 M HCl in dioxane (5 mL) gave the title compound in 66% yield (0.29 g). 1H NMR (400 MHz, CD3OD): δ 7.51 (dd, 1H), 7.36 (t, 1H), 7.26 (dd, 1H), 5.95 (d, 1H), 5.91 (d, 1H), 4.87 (m, 1H), 4.20 (m, 4H), 4.05 (m, 1H), 3.82 (dd, 1H), 3.77 (m, 2H), 3.37 (m, 2H), 3.23 (tt, 1H), 3.12 (m, 2H), 2.53 (s, 3H), 2.35 (m, 2H), 2.18 (m, 2H). MS-APCI (m/z+): 341, 385, 573.

Sources & evidence

ORD record
ord-cd0444e8729a4a33a98136cc52538435
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

Loading…