Triphenylphosphine → Orlistat

HRID 703678Notes

Reaction equation

HRID 703678 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 3034010OrlistatYield 26.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-01358dac1889497dbdbedb4611802538
Source dataset
uspto-grants-1991_01
Patent number
US04983746

Reaction notes

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