Ethanolamine → (4S)-4-Isobutyl-2-isopropyloxazolidine

HRID 276693

반응식

[CH3:1][O:2][C:3](=O)[C@H:4]([CH2:6][CH:7]([CH3:9])[CH3:8])[NH2:5].O[CH2:12][C@@H:13](N)[CH2:14]C(C)C.OCCN.C(=O)C(C)C>>[CH:13]([CH:1]1[NH:5][C@@H:4]([CH2:6][CH:7]([CH3:9])[CH3:8])[CH2:3][O:2]1)([CH3:14])[CH3:12]

참가 물질

반응물 4

HCID 700Ethanolamine

HCID 6561Isobutyraldehyde

HCID 65105(+)-L-Leucine methyl ester

HCID 111307L-Leucinol

생성물 1

HCID 45096513(4S)-4-Isobutyl-2-isopropyloxazolidine

실험 절차

(L)-Leucine methyl ester was reduced to (1S)-1-(hydroxymethyl)-3-methylbutylamine according to Method B1b, Step 2. The 2-hydroxyethylamine was reacted with isobutyraldehyde according to Method B4c, Step 1 to afford (4S)-2-isopropyl-4-isobutyl-1,3-oxazolidine. The oxazolidine was reduced according to Method B4c, Step 2 to give (1S)-1-(hydroxymethyl)-N-isobutyl-3-methylbutylamine. 4-Amino-3-ethylbenzonitrile was converted to 4-cyano-2-ethylformanilide according to Method A3a, Step 1. The formanilide was reacted with SOCl2 and SO2Cl2 according to Method A3a, Step 2 to give 4-cyano-2-ethylphenyl isocyanide dichloride. The substituted 2-hydroxyethylamine was reacted with 4-cyano-2-ethylphenyl isocyanide dichloride according to Method C7b to afford (4S)-2-(4-cyano-2-ethylphenylimino)-3,4-diisobutyl-1,3-oxazolidine.

출처 및 근거

ORD 기록: ord-c0e79a3d5de447a2ac3ee62c6d7421a8
출처 데이터셋: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US06353006B1

연결된 노트

불러오는 중…