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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1174266Generated: November 2, 2026

Tetrabutylammonium Fluoride → tert-butyl (1S,2S,4S)-1-benzyl-4-{[(benzyloxy)carbonyl]amino}-2-hydroxy-5-[4-(5-methyl-2-pyridinyl)phenyl]pentylcarbamate

https://huagongshe.com/reaction/1174266

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrabutylammonium FluorideHCID 2724141—
Reactanttert-butyl (1S,2S,4S)-1-benzyl-4-{[(benzyloxy)carbonyl]amino}-2-{[tert-butyl(dimethyl)silyl]oxy}-5-[4-(5-methyl-2-pyridinyl)phenyl]pentylcarbamateHCID 86726210—
SolventTetrahydrofuranHCID 8028—
Producttert-butyl (1S,2S,4S)-1-benzyl-4-{[(benzyloxy)carbonyl]amino}-2-hydroxy-5-[4-(5-methyl-2-pyridinyl)phenyl]pentylcarbamateHCID 8672621163%

Reaction Conditions

Temperature25 °C

Reaction Steps

The product from Example 92F (0.374 g, 0.517 mmol) was treated with TBAF solution in THF (2 mL, 1N), stirred at 25° C. for 16 hours, concentrated and partitioned between ethyl acetate and water. The organic phase was washed with brined, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-20% ethyl acetate in chloroform, to give the title compound (0.198 g, 63% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07834043B2
Source datasetuspto-grants-2010_11
ORD IDord-ca9d50903f7d4b0fa457cfeca0ef5225
Source noteuspto-grants-2010_11