Imidazole → (S)-N-Boc-2-amino-1(-tert-butyldimethylsilyloxy)-but-3-yne

HRID 366750Notes

Reaction equation

HRID 366750 reaction equation
[C:1]([NH:8][C@@H:9]([C:12]#[CH:13])[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>C(Cl)Cl>[C:1]([NH:8][C@@H:9]([C:12]#[CH:13])[CH2:10][O:11][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 21971753(S)-Tert-butyl (1-hydroxybut-3-YN-2-YL)carbamate

Product 1

HCID 21971752(S)-N-Boc-2-amino-1(-tert-butyldimethylsilyloxy)-but-3-yne

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-N-Boc-2-amino-1(-tert-butyldimethylsilyloxy)-but-3-yne was prepared by the treatment of (S)-N-Boc-2-amino-but-3-yn-1-ol (120 mg, 0.65 mmol) (Example 115A above) with imidazole (110 mg, 1.29 mmol) (Aldrich) and tert-butyldimethylsilyl chloride (120 mg, 0.77 mmol) (Fluka) in CH2Cl2 (10 mL) according to the procedure described above in Example 104B. (Yield 190 mg, 98%).

Sources & evidence

ORD record
ord-d1aec419498a471fa68307d92a7d3e87
Source dataset
uspto-grants-2000_10
Patent number
US06130239

Reaction notes

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