Propargyl alcohol → N-Desethyloxybutynin, (S)-

HRID 370365Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 370365
C1(C(C2C=CC=CC=2)(O)C(O)=O)CCCCC1.[CH3:18][CH2:19][N:20]([CH2:23][C:24]#[C:25][CH2:26][O:27][C:28]([C@:30]([OH:43])([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)=[O:29])CC.C(OC(Cl)=O)C(C)C.C(O)C#C.C(N(C(C)C#CO)CC1C=CC(OC)=CC=1)C.C1(C(C2CCCCC2)(O)C(OC#CCCN(CC)CC2C=CC(OC)=CC=2)=O)C=CC=CC=1.C(Cl)(=O)OC(Cl)C>>[C:31]1([C@:30]([CH:37]2[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]2)([OH:43])[C:28]([O:27][CH2:26][C:25]#[C:24][CH2:23][NH:20][CH2:19][CH3:18])=[O:29])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Komponenten

8

Edukt 7

HCID 7859Propargyl alcoholHCID 62365Isobutyl chloroformateHCID 97700(+-)-Cyclohexylphenylglycolic acidHCID 5213051-Chloroethyl chloroformateHCID 6098167AroxybutyninHCID 54413069N-ethyl-N-(4-methoxybenzyl)aminobutynyl phenylcyclohexyl-glycolateHCID 69648212N-ethyl-N-(4-methoxybenzyl)aminobutynol

Produkt 1

HCID 9945371N-Desethyloxybutynin, (S)-

Versuchsvorschrift

The method according to claim 1, wherein said single enantiomer of cyclohexylphenyl glycolic acid is the (S) enantiomer, said alkyl chloroformate is isobutylchloroformate, said sidechain propargyl alcohol derivative of formula (III) is N-ethyl-N-(4-methoxybenzyl)aminobutynol, and said single enantiomer of structure (II) is N-ethyl-N-(4-methoxybenzyl)aminobutynyl phenylcyclohexyl-glycolate, which is treated with α-chloroethyl carbonochloridate to provide (S)-4-ethylamino-2-butynyl phenylcyclohexylglycolate.

Quellen und Nachweise

ORD-Eintrag
ord-11bf3b40865d45ab89832788d86873e8
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140529

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