Hydrochloric Acid → HCID 11399515, compound

HRID 915285Notes

Reaction equation

HRID 915285 reaction equation
[C:1]([N:4]([CH2:28][C@@H:29]1[O:33][C:32](=[O:34])[N:31]([C:35]2[CH:40]=[CH:39][C:38]([CH:41]3[CH2:46][CH2:45][S:44](=[O:48])(=[O:47])[CH2:43][CH2:42]3)=[C:37]([F:49])[CH:36]=2)[CH2:30]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:27])[C@@H:11]([NH:19]C(OC(C)(C)C)=O)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:6])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1.[ClH:58]>C1COCC1>[ClH:58].[C:1]([N:4]([CH2:28][C@@H:29]1[O:33][C:32](=[O:34])[N:31]([C:35]2[CH:40]=[CH:39][C:38]([CH:41]3[CH2:42][CH2:43][S:44](=[O:47])(=[O:48])[CH2:45][CH2:46]3)=[C:37]([F:49])[CH:36]=2)[CH2:30]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:27])[C@@H:11]([NH2:19])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:6])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 11331500HCID 11331500, compound

Product 1

HCID 11399515HCID 11399515, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2(S)-tert-Butoxycarbonylamino-3-phenyl-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 (12 g) (0.78 g, 1.1 mmol), anisole (0.5 mL) and THF (20 mL) are cooled to 0° C. Hydrogen chloride (4 M in dioxane, 8 mL, 33.1 mmol) is added in a dropwise manner. After complete addition, the ice-bath is removed and 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 63% yield (0.45 g). 1H NMR (400 MHz, CD3OD): δ 7.50 (dd, 1H), 7.39-7.24 (m, 7H), 6.02 (d, 1H), 5.97 (d, 1H), 4.86 (m, 1H), 4.50 (dd, 1H), 4.18 (m, 2H), 4.09 (dd, 1H), 3.83 (dd, 1H), 3.35 (m, 3H), 3.21 (m, 2H), 3.11 (m, 2H), 2.53 (s, 3H), 2.34 (m, 2H), 2.16 (m, 2H). MS-APCI (m/z+): 341, 385, 606.

Workup

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

Sources & evidence

ORD record
ord-5381ec0d57b94cd99932111c14fa8282
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

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