Hydrochloric Acid → HCID 11215730, compound

HRID 915297Notes

Reaction equation

HRID 915297 reaction equation
[C:1]([N:4]([CH2:26][C@@H:27]1[O:31][C:30](=[O:32])[N:29]([C:33]2[CH:38]=[CH:37][C:36]([CH:39]3[CH2:44][CH2:43][S:42](=[O:46])(=[O:45])[CH2:41][CH2:40]3)=[C:35]([F:47])[CH:34]=2)[CH2:28]1)[C:5]([O:7][CH:8]([O:10][C:11](=[O:25])[C@@H:12]([NH:17]C(OC(C)(C)C)=O)[C@@H:13]([CH3:16])[CH2:14][CH3:15])[CH3:9])=[O:6])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1.C1COCC1.[ClH:61]>C(OCC)C>[ClH:61].[C:1]([N:4]([CH2:26][C@@H:27]1[O:31][C:30](=[O:32])[N:29]([C:33]2[CH:38]=[CH:37][C:36]([CH:39]3[CH2:40][CH2:41][S:42](=[O:45])(=[O:46])[CH2:43][CH2:44]3)=[C:35]([F:47])[CH:34]=2)[CH2:28]1)[C:5]([O:7][CH:8]([O:10][C:11](=[O:25])[C@@H:12]([NH2:17])[C@@H:13]([CH3:16])[CH2:14][CH3:15])[CH3:9])=[O:6])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 8028TetrahydrofuranHCID 11445358HCID 11445358, compound

Product 1

HCID 11215730HCID 11215730, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

2(S)-tert-butoxycarbonylamino-3(S)-methyl-pentanoic acid 1-(acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5(R)-ylmethyl}-carbamoyloxy)-ethyl ester (12j) (1.00 g, 1.46 mmol), anisole (0.24 g, 2.188 mmol) and THF (30 mL) are cooled in an ice bath. Hydrochloric acid (4 N in dioxane, 10.94 mL) is added dropwise. The solution is stirred in an ice bath for 30 min and then at RT for 4 h. The reaction mixture is re-cooled to 0° C. and ethyl ether is added. The resulting solids are collected by filtration and washed with a cold ethyl ether/ethyl acetate mixture to afford the title compound. Isolated yield: 64%. 1H NMR (400 MHz, DMSO-d6): δ 8.46 (br s, 3H), 7.43-7.39 (m, 1H), 7.36 (t, 1H), 7.22 (d, 1H), 6.85-6.79 (m, 1H), 4.77-4.71 (m, 1H), 4.13-4.00 (m, 2H), 3.96 (dd, 1H),3.88-3.84 (m, 1H), 3.80-3.74 (m, 1H), 3.51-3.28 (m, partially obscured by water, 2H), 3.18-3.12 (m, 1H), 3.04 (d, 2H), 2.40 (d, 3H), 2.08 (q, 2H), 1.97-1.93 (m, 2H), 1.90-1.84 (br m, 1H), 1.50 (dd, 3H), 1.44-1.36 (m, 1H), 1.26-1.14 (m, 1H), 0.88 (dd, 3H), 0.84-0.79 (m, 3H).

Workup

  1. waitat RT for 4 h
  2. filtrationThe resulting solids are collected by filtration
  3. washwashed with a cold ethyl ether/ethyl acetate mixture

Sources & evidence

ORD record
ord-5609822d9a544e0a9b32fbb5103831d1
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

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