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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 926009Generated: October 30, 2026

Tetrabutylammonium Fluoride → (1aR,3aR,5R,7aR,15aS,Z)-methyl 5-hydroxy-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylate

https://huagongshe.com/reaction/926009

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrabutylammonium FluorideHCID 2724141—
Reactant(1aR,3aR,5R,7aR,15aS,Z)-methyl 5-(tert-butyldiphenylsilyloxy)-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylateHCID 131735010—
SolventTetrahydrofuranHCID 8028—
Product(1aR,3aR,5R,7aR,15aS,Z)-methyl 5-hydroxy-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylateHCID 69915043—

Reaction Steps

To a solution of compound 42 (0.6 mmol) in dry THF (12 mL) was added dropwise a solution of tetrabutylammonium fluoride (1M in THF, 12 mL). The reaction was stirred at room temperature overnight, and then concentrated. The residue was dissolved in MeOH and purified by semi preparative HPLC (RP18) to yield compound 43, which was used without further purification directly in the next step. MS (ESI, EI+): m/z=379 (MH+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09284307B2
Source datasetuspto-grants-2016_03
ORD IDord-eb5f664767214c3197153e4dbb6ab6ee
Source noteuspto-grants-2016_03