Imidazole → (2R,3R)-N-Boc-3-amino-2-(-tert-butyldimethylsilyloxy)-pent-4-yne

HRID 380916Notes

Reaction equation

HRID 380916 reaction equation
[C:1]([NH:8][C@H:9]([C:13]#[CH:14])[C@H:10]([OH:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl>[C:1]([NH:8][C@H:9]([C:13]#[CH:14])[C@H:10]([O:12][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH3:11])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 21971742(2R,3R)-N-Boc-3-amino-pent-4-yne-2-ol

Product 1

HCID 21971741(2R,3R)-N-Boc-3-amino-2-(-tert-butyldimethylsilyloxy)-pent-4-yne

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R,3R)-N-Boc-3-amino-2-(-tert-butyldimethylsilyloxy)-pent-4-yne was prepared by the treatment of (2R,3R)-N-Boc-3-amino-pent-4-yn-2-ol (1.10 g, 5.02 mmol) (Example 117A above) with imidazole (680 mg, 10.04 mmol) and tert-butyldimethylsilyl chloride (800 mg, 5.52 mmol) in 35 mL of CH2Cl2. After 24 hrs stirring at room temperature, the mixture was concentrated to a residue which upon silica gel column chromatography with a 0-20% EtOAc in hexanes gradient yielded (2R,3R)-N-Boc-3-amino-2-(-tert-butyldimethylsilyloxy)-pent-4-yne. (Yield 1.30 g, 83%).

Workup

  1. concentrationthe mixture was concentrated to a residue which upon silica gel column chromatography with a 0-20% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-366c90a83ac142a38d110d0cb6ec2177
Source dataset
uspto-grants-2001_10
Patent number
US06303793B1

Reaction notes

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