Triphenylphosphine → Orlistat

HRID 703678

반응식

HRID 703678 반응식
[CH2:1]([C@H:7]1[C@H:10]([CH2:11][C@H:12]([OH:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[O:9][C:8]1=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:45]([NH:47][C@H:48]([C:53](O)=[O:54])[CH2:49][CH:50]([CH3:52])[CH3:51])=[O:46].N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:1]([C@@H:7]1[C:8](=[O:25])[O:9][C@H:10]1[CH2:11][C@@H:12]([O:24][C:53](=[O:54])[C@H:48]([CH2:49][CH:50]([CH3:52])[CH3:51])[NH:47][CH:45]=[O:46])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9880216N-FormylleucineHCID 104282483-Hexyl-4-((R)-2-hydroxytridecyl)-2-oxetanone, (3S,4S)-

생성물 1

HCID 3034010Orlistat수율 26.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 100 mg of rac-3-hexyl -4-(2-hydroxy-tridecyl)-2-oxetanone(2R,3S,4S:2S,3R,4R) or of 100 mg of (3S,4S)-3-hexyl-4-[(R)-2-hydroxytridecyl]-2-oxetanone, 74 mg of triphenylphosphine and 45 mg of N-formyl-L-leucine in 2 ml of THF are added dropwise while stirring 44.3 μl of diethyl azodicarboxylate. After stirring overnight the organic phase is evaporated in vacuo and the residue is purified by chromatography on silica gel with toluene-ethyl acetate (9:1). There are obtained 20 or 37 mg of N-formyl-L-leucine (S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester, [α]D20 =-33° C. (c=0.36, CHCL3).

후처리

  1. customis evaporated in vacuo
  2. customthe residue is purified by chromatography on silica gel with toluene-ethyl acetate (9:1)

출처 및 근거

ORD 기록
ord-01358dac1889497dbdbedb4611802538
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04983746

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