Ethanolamine → (4S)-2-(4-(methoxycarbonyl)-2-methylphenylimino)-4-isobutyl-1,3-thiazolidine

HRID 276455노트

반응식

O[CH2:2][C@@H:3]([NH2:8])[CH2:4][CH:5]([CH3:7])[CH3:6].COC(=O)[C@H](CC(C)C)N.OCCN.[CH3:23][O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[S:35])=[C:29]([CH3:36])[CH:28]=1)=[O:26]>>[CH3:23][O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]2[NH:8][C@@H:3]([CH2:4][CH:5]([CH3:7])[CH3:6])[CH2:2][S:35]2)=[C:29]([CH3:36])[CH:28]=1)=[O:26]

참가 물질

반응물 4

HCID 700Ethanolamine

HCID 65105(+)-L-Leucine methyl ester

HCID 111307L-Leucinol

HCID 18316033Methyl 4-isothiocyanato-3-methylbenzoate

생성물 1

HCID 178498123(4S)-2-(4-(methoxycarbonyl)-2-methylphenylimino)-4-isobutyl-1,3-thiazolidine

실험 절차

(1S)-1-(Hydroxymethyl)-3-methyl butylamine was made from (L)-leucine methyl ester as described in Method B1b. The 2-hydroxyethylamine was converted to (1S)-1-(chloromethyl)-3-methylbutanammonium chloride as described in Method B7a. 4-(Methoxycarbonyl)-2-methylphenyl isothiocyanate was reacted with (1S)-1-(chloromethyl)-3-methylbutanammonium chloride according to Method C1a to give (4S)-2-(4-(methoxycarbonyl)-2-methylphenylimino)-4-isobutyl-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2a to give (4S)-2-(4-(methoxycarbonyl)-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine.

출처 및 근거

ORD 기록: ord-bd6905299a5f4abb92b094b1cb782c11
출처 데이터셋: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US06353006B1

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