Water → HCID 178464708, compound

HRID 2389089Notes

Reaction equation

HRID 2389089 reaction equation
[CH:1]1([CH:6]2[CH2:11][CH2:10][CH:9]([O:12][C:13]3[C:14]([C:30]([F:33])([F:32])[F:31])=[C:15]4[C:20](=[CH:21][CH:22]=3)[CH:19]=[C:18]([C@:23]3([CH3:29])[CH2:27][O:26]C(=O)[NH:24]3)[CH:17]=[CH:16]4)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+].O>>[NH2:24][C@@:23]([C:18]1[CH:17]=[CH:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]([O:12][C@H:9]3[CH2:10][CH2:11][C@H:6]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH2:7][CH2:8]3)[C:14]=2[C:30]([F:32])([F:33])[F:31])[CH:19]=1)([CH3:29])[CH2:27][OH:26]

Participants

4

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67411587HCID 67411587, compound

Product 1

HCID 178464708HCID 178464708, compoundYield 86.1%

Procedure

The compound was prepared in a manner similar as to that described above (R)-4-[6-(4-Cyclopentyl-cyclohexyloxy)-5-trifluoromethyl-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (15 mg, 0.000032 mol), (0.14 g, 0.0030 mol), 4.2 M lithium hydroxide, monohydrate in water (0.13 mL, 0.00055 mol) to give 12 mg of the desired product as a white solid (81%). ESI-MS: 419 (M-16)+. 1H NMR (400 MHz, MeOD) δ=8.64-8.50 (m, 1 H), 8.17-7.98 (m, 2 H), 7.98-7.87 (m, 1 H), 7.73-7.62 (m, 1 H), 7.50-7.40 (m, 1 H), 4.84-4.76 (m, 2 H), 3.80-3.58 (m, 2 H), 2.12-1.96 (m, 2 H), 1.85-1.42 (m, 18 H), 1.21-1.05 (m, 2 H).

Sources & evidence

ORD record
ord-d1d0d8d843a44b92a34fe27b4a16eb17
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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