Ethanol → (R)-2-amino-2-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)propan-1-ol

HRID 2389112Notes

Reaction equation

HRID 2389112 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[CH:22]=[C:21]([C@:26]2([CH3:32])[CH2:30][O:29]C(=O)[NH:27]2)[CH:20]=[CH:19]3)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.O.[OH-].[Li+]>>[NH2:27][C@@:26]([C:21]1[CH:20]=[CH:19][C:18]2[C:23](=[CH:24][CH:25]=[C:16]([S:15][C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:10]=3)[CH:17]=2)[CH:22]=1)([CH3:32])[CH2:30][OH:29]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 67413241(R)-4-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 46196286(R)-2-amino-2-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)propan-1-olYield 92.1%

Procedure

(R)-4-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)-4-methyloxazolidin-2-one (30.0 mg, 0.0000679 mol) was dissolved in ethanol (2 mL, 0.03 mol) and water (0.8 mL, 0.05 mol) then lithium hydroxide (17 mg, 0.00072 mol) was added and was heated to reflux overnight. LCMS shows no SM and a new peak at 1.51 399.17 ([M-NH2]+, 100). After concentration, the residue was taken up into methylene chloride and water. The aqueous layer was extracted with methylene chloride and concentrated. Column chromatography with MeOH/methylene chloride gave (R)-2-amino-2-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)propan-1-ol as a white solid (26.0 mg, 92%). LCMS 1.51 399.17 ([M-NH2]+, 100%). 1H NMR (400 MHz, MeOD) δ=7.95 (br. s., 1 H), 7.89-7.76 (m, 3 H), 7.64 (d, J=8.6 Hz, 1 H), 7.43-7.20 (m, 7 H), 6.98-6.87 (m, 3 H), 5.00 (br. s., 2 H), 3.84-3.77 (m, 1 H), 3.77-3.69 (m, 1 H), 1.60 (s., 3 H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. concentrationAfter concentration
  4. extractionThe aqueous layer was extracted with methylene chloride
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7b19a368819a4a5b8a0f3be4e57cbbd5
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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