HCID 178461141, compound → HCID 178461145, compound

HRID 2389198Notes

Reaction equation

HRID 2389198 reaction equation
[F:1][C:2]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C@:22]2([CH3:28])[CH2:26][O:25]C(=O)[NH:23]2)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([F:4])[CH3:3]>CCO.O>[NH2:23][C@@:22]([C:17]1[CH:16]=[CH:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([O:11][C@H:8]3[CH2:9][CH2:10][C@H:5]([C:2]([F:1])([F:4])[CH3:3])[CH2:6][CH2:7]3)[CH:13]=2)[CH:18]=1)([CH3:28])[CH2:26][OH:25]

Participants

4

Reactant 1

HCID 178461141HCID 178461141, compound

Product 1

HCID 178461145HCID 178461145, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

(R)-4-(6-(cis-4-(1,1-Difluoroethyl)cyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one (32 mg, 0.083 mmol) was dissolved in EtOH (5 mL). Then LION (60 mg, 2.5 mmol, 30.0 eq.) in 1 mL water was added to the mixture. The mixture was heated to 80° C. and stirred for 15 h. LCMS showed starting material was gone. Solvent was removed. DCM was added and filtered. The filtrate was concentrated and purified by silica gel chromatography using DCM/methanol (10/1) to give product (12 mg, 40%) as a slight yellow solid. EDI-MS (M-NH2): 347.0. HPLC: 98.82%. 1H NMR (400 MHz, CDCl3) δ 7.82 (s, 1H), 7.72-7.66 (m, 2H), 7.49 (d, 1H), 7.10 (d, 2H), 4.30-4.27 (m, 1H), 3.78-3.68 (AB, 2H), 3.18 (b, 3H), 2.32-2.30 (m, 2H), 2.04-1.99 (m, 2H), 1.63-1.19 (m, 11H).

Workup

  1. customSolvent was removed
  2. additionDCM was added
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-7e491bbd0b244feda4e6b3239aad8f04
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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