Lithium Hydroxide → HCID 56971595, compound

HRID 1508603Notes

Reaction equation

HRID 1508603 reaction equation
[N:1]1([C:5]2[N:10]=[C:9]([CH2:11][N:12]3[C@@H:16]([CH3:17])[C@@H:15]([C:18]4[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=4)[O:14][C:13]3=[O:26])[C:8]([C:27]3[CH:28]=[C:29]([C:35]4[CH:40]=[CH:39][C:38]([C:41]([O:43]C)=[O:42])=[CH:37][C:36]=4[CH3:45])[CH:30]=[CH:31][C:32]=3[O:33][CH3:34])=[CH:7][N:6]=2)[CH2:4][CH2:3][CH2:2]1.[Li+].[OH-].C(O)(C(F)(F)F)=O>O1CCOCC1>[N:1]1([C:5]2[N:10]=[C:9]([CH2:11][N:12]3[C@@H:16]([CH3:17])[C@@H:15]([C:18]4[CH:19]=[C:20]([Cl:25])[CH:21]=[C:22]([Cl:24])[CH:23]=4)[O:14][C:13]3=[O:26])[C:8]([C:27]3[CH:28]=[C:29]([C:35]4[CH:40]=[CH:39][C:38]([C:41]([OH:43])=[O:42])=[CH:37][C:36]=4[CH3:45])[CH:30]=[CH:31][C:32]=3[O:33][CH3:34])=[CH:7][N:6]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 86704649HCID 86704649, compound

Product 1

HCID 56971595HCID 56971595, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To methyl 3′-[2-(azetidin-1-yl)-4-{[(4S,5R)-5-(3,5-dichlorophenyl)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}pyrimidin-5-yl]-4′-methoxy-2-methylbiphenyl-4-carboxylate (78 mg, 0.121 mmol) in dioxane (2.4 mL) was added LiOH (0.5 M, 1.2 mL, 0.605 mmol). The reaction was heated to 60° C. for 1 hour before cooling and acidifying with TFA. The volatiles were removed and the crude material was purified by reverse phase HPLC to yield 3′-[2-(azetidin-1-yl)-4-{[(4S,5R)-5-(3,5-dichlorophenyl)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}pyrimidin-5-yl]-4′-methoxy-2-methylbiphenyl-4-carboxylic acid (70 mg, 0.110 mmol). LCMS calc.=633.2. found=−633.3. 1H NMR (CDCl3, 500 MHz) 8.19 (s, 1H), 7.98 (m, 2H), 7.33 (m, 3H), 7.15 (m, 3H), 7.04 (d, J=8.6 Hz, 1H), 5.42 (br s, 1H), 4.75 (br s, 1H), 4.23 (m, 5H), 4.01 (br s, 1H), 3.87 (s, 3H), 2.43 (m, 2H), 2.36 (s, 3H), 0.73 (s, 3H). RTA=4.43 nM

Workup

  1. temperaturebefore cooling
  2. customThe volatiles were removed
  3. customthe crude material was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-9b68c33456134dbb9123ddd9416dad4d
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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