p-Toluenesulfonic acid monohydrate → (S)-Tert-butyl (1-hydroxybut-3-YN-2-YL)carbamate

HRID 380911Notes

Reaction equation

HRID 380911 reaction equation
[C:1]([N:8]1[C@@H:12]([C:13]#[CH:14])[CH2:11][O:10]C1(C)C)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.O>[C:1]([NH:8][C@@H:12]([C:13]#[CH:14])[CH2:11][OH:10])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 11160457tert-Butyl (4S)-4-ethynyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Product 1

HCID 21971753(S)-Tert-butyl (1-hydroxybut-3-YN-2-YL)carbamate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of (S)-N-Boc-2,2-dimethyl-4-ethynyl-oxazolidine (200 mg, 0.89 mmol) (Example 93A above) in a mixture of MeOH (25 mL) and water (2 mL) was treated with ρ-toluenesulfonic acid monohydrate (16 mg, 0.09 mmol) according to the procedure that described above in Example 104A. (Yield 120 mg, 73%).

Sources & evidence

ORD record
ord-20912e66d73b489ab6b8e1008740ba81
Source dataset
uspto-grants-2001_10
Patent number
US06303793B1

Reaction notes

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