Hydrochloric Acid → HCID 11204129, compound

HRID 915282Notes

Reaction equation

HRID 915282 reaction equation
[C:1]([N:4]([CH2:24][C@@H:25]1[O:29][C:28](=[O:30])[N:27]([C:31]2[CH:36]=[CH:35][C:34]([CH:37]3[CH2:42][CH2:41][S:40](=[O:44])(=[O:43])[CH2:39][CH2:38]3)=[C:33]([F:45])[CH:32]=2)[CH2:26]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:23])[C@H:11]([NH:15]C(OC(C)(C)C)=O)[CH:12]([CH3:14])[CH3:13])=[O:6])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1.C1COCC1.[ClH:59]>O1CCOCC1>[ClH:59].[C:1]([N:4]([CH2:24][C@@H:25]1[O:29][C:28](=[O:30])[N:27]([C:31]2[CH:36]=[CH:35][C:34]([CH:37]3[CH2:42][CH2:41][S:40](=[O:43])(=[O:44])[CH2:39][CH2:38]3)=[C:33]([F:45])[CH:32]=2)[CH2:26]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:23])[C@H:11]([NH2:15])[CH:12]([CH3:13])[CH3:14])=[O:6])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 8028TetrahydrofuranHCID 11158084HCID 11158084, compound

Product 1

HCID 11204129HCID 11204129, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Following general procedure G, 2(R)-tert-Butoxycarbonylamino-3-methyl-butyric acid (acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5(R)-ylmethyl}-carbamoyloxy)-methyl ester (12d) (0.89 g, 1.35 mmol), anisole (0.12 mL), THF (25 mL), and 4 M HCl in dioxane (10 mL) gave the title compound in 51% yield (0.41 g). 1H NMR (400 MHz, DMSO): δ 8.52 (br s, 3H), 7.47 (dd, 1H), 7.39 (t, 1H), 7.28 (dd, 1H), 5.98 (d, 1H), 5.93 (d, 1H), 4.80 (m, 1H), 4.14 (m, 2H), 4.03 (d, 1H), 3.90 (dd, 1H), 3.82 (dd, 1H), 3.39 (m, 2H), 3.20 (tt, 1H), 3.10 (m, 2H), 2.47 (s, 3H), 2.17 (m, 3H), 2.04 (m, 2H), 0.98 (d, 3H), 0.96 (d, 3H), MS-APCI (m/z+): 558.

Sources & evidence

ORD record
ord-81c42ef4e1784e59827ad7598a2953ca
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

Loading…