p-Toluenesulfonic acid → HCID 57544576, compound

HRID 1254364Notes

Reaction equation

HRID 1254364 reaction equation
[CH3:1][O:2][C:3]([CH3:20])([CH3:19])[CH2:4][C@H:5]1[CH2:9][O:8]C(C)(C)[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].CC1C=CC(S(O)(=O)=O)=CC=1>CO>[OH:8][CH2:9][C@@H:5]([NH:6][C:12](=[O:13])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:4][C:3]([O:2][CH3:1])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 57544970HCID 57544970, compound

Product 1

HCID 57544576HCID 57544576, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-tert-butyl 4-(2-methoxy-2-methylpropyl)-2,2-dimethyl-oxazolidine-3-carboxylate (1.2 g, 3.40 mmol) in MeOH (5 mL) at rt, there was added 4-methylbenzenesulfonic acid (0.65 g, 3.40 mmol). The resulting solution was stirred until no starting material remained (˜1 h). Solvent was removed under vacuum, and the residue was redissolved in acetone (3 mL) and H2O (1 mL). Excess K2CO3 was added to keep the solution basic, followed by (Boc)2O. The mixture was stirred for 20 min, acetone was removed under vacuum, and the aqueous solution was extracted with CH2Cl2 (4×5 mL). After concentration, the residue was purified by flash column chromatography to give (S)-tert-butyl 1-hydroxy-4-methoxy-4-methylpentan-2-ylcarbamate (0.76 g, 78%, 2 steps). 1H NMR (400 MHz, CDCl3): 5.38 (br, 1 H), 3.78 (m, 1 H), 3.66 (m, 1 H), 3.56 (m, 1 H), 3.20 (s, 3 H), 1.66 (m, 2 H), 1.62 (br, 1 H), 1.44 (s, 9 H), 1.20 (s, 6 H); MS m/z 248 (M+H+).

Workup

  1. custom(˜1 h)
  2. customSolvent was removed under vacuum
  3. dissolutionthe residue was redissolved in acetone (3 mL)
  4. additionExcess K2CO3 was added
  5. stirringThe mixture was stirred for 20 min
  6. customacetone was removed under vacuum
  7. extractionthe aqueous solution was extracted with CH2Cl2 (4×5 mL)
  8. concentrationAfter concentration
  9. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-702e22db3f3244b28f6672104abdbd9b
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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