Acetic Anhydride → HCID 21639731, compound

HRID 1032284Notes

Reaction equation

[CH:1]([N-]C(C)C)(C)[CH3:2].[Li+].[CH2:9]([Si:11]([CH2:21]C)([CH2:19]C)[C:12]1[O:16][CH:15]=[C:14](C=O)[CH:13]=1)C.C(OC(=O)C)(=O)C>>[CH2:1]([C:13]1[CH:14]=[CH:15][O:16][C:12]=1[Si:11]([CH3:9])([CH3:19])[CH3:21])[CH3:2]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 2724682Lithium diisopropylamide

HCID 108784383-Furancarboxaldehyde, 5-(triethylsilyl)-

Product 1

HCID 21639731HCID 21639731, compound

Procedure

Reacting 1-N-acetyl-20-(-N',N'-dimethyl)decyl diamine (prepare from 1,10-(-N',N'-dimethyl)decyl diamine with acetyl chloride) with lithium diisopropylamide, followed by 5-triethylsilyl-3-furaldehyde and acetic anhydride gives 4-[1-acetoxy-2(N-10-N',N'-dimethyl)aminodecyl)amido]ethyl-2-trimethylsilylfuran. Treatment of this intermediate with excess iodomethane followed by singlet oxygen oxidation gives r-[1-acetoxy-2-(N-10-(N',N',N'-trimethyl)aminodecyl)amido]ethyl-5-hydroxy-2(5H)-furanone.

Sources & evidence

ORD record: ord-3251d97358714fb68e2e9be29e73a3ab
Source dataset: uspto-grants-1990_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04957917

Reaction notes

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