Hydrochloric Acid → HCID 11169416, compound

HRID 915284Notes

Reaction equation

HRID 915284 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])[C@@H:11]([NH:16]C(OC(C)(C)C)=O)[C@@H:12]([CH3:15])[CH2:13][CH3:14])=[O:6])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1.[ClH:55]>C1COCC1>[ClH:55].[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])[C@@H:11]([NH2:16])[C@@H:12]([CH3:15])[CH2:13][CH3:14])=[O:6])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 11433843HCID 11433843, compound

Product 1

HCID 11169416HCID 11169416, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2(S)-tert-Butoxycarbonylamino-3(S)-methyl-pentanoic acid (acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5(R)-ylmethyl}-carbamoyloxy)-methyl ester (12f) (0.82 g, 1.23 mmol), anisole (0.2 mL) and THF (25 mL) are cooled to 0° C. Hydrogen chloride (4 M in dioxane, 9 mL, 36.8 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-third 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 dried under vacuum to give the title compound in 52% yield (0.39 g). 1H NMR (400 MHz, CD3OD): δ 7.51 (d, 1H), 7.36 (t, 1H), 7.26 (d, 1H), 6.05 (d, 1H), 6.00 (d, 1H), 4.87 (m, 1H), 4.20 (m, 3H), 4.09 (dd, 1H), 3.84 (dd, 1H), 3.37 (m, 2H), 3.23 (tt, 1H), 3.11 (m, 2H), 2.54 (s, 3H), 2.34 (m, 2H), 2.17 (m, 2H), 2.06 (m, 1H), 1.56 (m, 1H), 1.39 (m, 1H), 1.06 (d, 3H), 1.00 (t, 3H). MS-APCI (m/z+): 341, 385, 572.

Workup

  1. additionAfter complete addition
  2. customthe ice-bath is removed
  3. concentrationUnder reduced pressure, the mixture is concentrated to one-third 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
  9. customdried under vacuum

Sources & evidence

ORD record
ord-6de689066a5649b1b04db331be2a09ec
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

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