Hydrochloric Acid → HCID 11180399, compound

HRID 915279Notes

Reaction equation

HRID 915279 reaction equation
[C:1]([N:4]([CH2:21][C@@H:22]1[O:26][C:25](=[O:27])[N:24]([C:28]2[CH:33]=[CH:32][C:31]([CH:34]3[CH2:39][CH2:38][S:37](=[O:41])(=[O:40])[CH2:36][CH2:35]3)=[C:30]([F:42])[CH:29]=2)[CH2:23]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:20])[CH2:11][NH:12]C(OC(C)(C)C)=O)=[O:6])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1.C1COCC1.[ClH:56]>O1CCOCC1>[ClH:56].[C:1]([N:4]([CH2:21][C@@H:22]1[O:26][C:25](=[O:27])[N:24]([C:28]2[CH:33]=[CH:32][C:31]([CH:34]3[CH2:39][CH2:38][S:37](=[O:40])(=[O:41])[CH2:36][CH2:35]3)=[C:30]([F:42])[CH:29]=2)[CH2:23]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:20])[CH2:11][NH2:12])=[O:6])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 8028TetrahydrofuranHCID 11238923HCID 11238923, compound

Product 1

HCID 11180399HCID 11180399, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Following General procedure G, except that the entire reaction is performed at RT. (R)-Tert-butoxycarbonylamino-acetic acid (acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamoyloxy)-methyl ester (12a) (0.24 g, 0.39 mmol), anisole (0.5 mL), THF (7.3 mL), and 4 M HCl in dioxane (3 mL) gave the title compound in 72% yield (0.16 g). 1H NMR (400 MHz, DMSO): δ 8.39 (br d, 3H), 7.47 (dd, 1H), 7.39 (t, 1H), 7.28 (dd, 1H), 5.93 (m, 2H), 4.80 (m, 1H), 4.14 (m, 2H), 3.92 (m, 3H), 3.82 (m, 1H), 3.37 (m, 2H), 3.20 (m, 1H), 3.10 (m, 2H), 2.47 (s, 3H), 2.16 (m, 2H), 2.04 (m, 2H). MS-APCI (m/z+): 516, 616.

Workup

  1. customexcept that the entire reaction
  2. customis performed at RT

Sources & evidence

ORD record
ord-fb34fed0c1ee4a3ab52a4b89b2fef621
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

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