Hydrochloric Acid → HCID 11203843, compound

HRID 915280Notes

Reaction equation

HRID 915280 reaction equation
[C:1]([N:4]([CH2:22][C@@H:23]1[O:27][C:26](=[O:28])[N:25]([C:29]2[CH:34]=[CH:33][C:32]([CH:35]3[CH2:40][CH2:39][S:38](=[O:42])(=[O:41])[CH2:37][CH2:36]3)=[C:31]([F:43])[CH:30]=2)[CH2:24]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:21])[C@@H:11]([NH:13]C(OC(C)(C)C)=O)[CH3:12])=[O:6])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1.[ClH:52]>C1COCC1>[ClH:52].[C:1]([N:4]([CH2:22][C@@H:23]1[O:27][C:26](=[O:28])[N:25]([C:29]2[CH:34]=[CH:33][C:32]([CH:35]3[CH2:40][CH2:39][S:38](=[O:41])(=[O:42])[CH2:37][CH2:36]3)=[C:31]([F:43])[CH:30]=2)[CH2:24]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:21])[C@@H:11]([NH2:13])[CH3:12])=[O:6])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 11250634HCID 11250634, compound

Product 1

HCID 11203843HCID 11203843, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of the 2(S)-tert-butoxycarbonylamino-propionic acid (acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5(R)-ylmethyl}-carbamoyloxy)-methyl ester (12b) (0.98 g, 1.56 mmol), anisole (1 mL) and THF (30 mL), is added hydrogen chloride (4 M in dioxane, 11 mL, 46.8 mmol) in a dropwise manner. The mixture is stirred at RT overnight. Under reduced pressure, the mixture is concentrated to one-half of its original volume. Ether is then added dropwise to the mixture while stirring, resulting in the formation of a solid. The solid is collected via filtration, rinsed with ether and ethyl acetate, and dried under vacuum to give the title compound in 38% yield (0.34 g). 1H NMR (400 MHz, CD3OD): δ 7.51 (dd, 1H), 7.37 (t, 1H), 7.26 (dd, 1H), 6.02 (ABq, 2H), 4.87 (m, 1H), 4.29 (app q, 1H), 4.19 (m, 2H), 4.10 (dd, 1H), 3.83 (dd, 1H), 3.37 (m, 2H), 3.23 (tt, 1H),3.12 (m, 2H), 2.54 (s, 3H), 2.35 (m, 2H), 2.18 (m, 2H), 1.59 (d, 3H). MS-APCI (m/z+): 530.

Workup

  1. concentrationUnder reduced pressure, the mixture is concentrated to one-half of its original volume
  2. additionEther is then added dropwise to the mixture
  3. stirringwhile stirring
  4. customresulting in the formation of a solid
  5. filtrationThe solid is collected via filtration
  6. washrinsed with ether and ethyl acetate
  7. customdried under vacuum

Sources & evidence

ORD record
ord-4e1a753fbe954a0ab990efd760ae5441
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

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