Triphenylphosphine → N-{2-[(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-{(3-methylbutyl)[(4-nitrophenyl)sulfonyl]amino}butyl]phenyl}-Nalpha-(methoxycarbonyl)-beta-phenyl-L-phenylalaninamide

HRID 714132Notes

Reaction equation

HRID 714132 reaction equation
[Si:1]([O:18][CH2:19][C@@H:20]([NH:51][S:52]([C:55]1[CH:60]=[CH:59][C:58]([N+:61]([O-:63])=[O:62])=[CH:57][CH:56]=1)(=[O:54])=[O:53])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][C:30](=[O:50])[C@H:31]([CH:37]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[NH:32][C:33]([O:35][CH3:36])=[O:34])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:83](O)[CH2:84][CH:85]([CH3:87])[CH3:86].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Si:1]([O:18][CH2:19][C@@H:20]([N:51]([CH2:83][CH2:84][CH:85]([CH3:87])[CH3:86])[S:52]([C:55]1[CH:56]=[CH:57][C:58]([N+:61]([O-:63])=[O:62])=[CH:59][CH:60]=1)(=[O:53])=[O:54])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][C:30](=[O:50])[C@H:31]([CH:37]([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[NH:32][C:33]([O:35][CH3:36])=[O:34])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 31260Isoamyl AlcoholHCID 5363146Diisopropyl azodicarboxylateHCID 86708031N-{2-[(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-{[(4-nitrophenyl)sulfonyl]amino}butyl]phenyl}-Nalpha-(methoxycarbonyl)-beta-phenyl-L-phenylalaninamide

Product 1

HCID 86708032N-{2-[(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-{(3-methylbutyl)[(4-nitrophenyl)sulfonyl]amino}butyl]phenyl}-Nalpha-(methoxycarbonyl)-beta-phenyl-L-phenylalaninamideYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-{2-[(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-{[(4-nitrophenyl)sulfonyl]amino}butyl]phenyl}-Nα-(methoxycarbonyl)-β-phenyl-L-phenylalaninamide (9, 160 mg, 0.181 mmol), Ph3P (149 mg, 0.568 mmol) and isoamyl alcohol (89 mg, 1.01 mmol) (or any other suitable alcohol) in THF (1.5 ml) stirred at external temperature of 0° C. under N2 atmosphere, was treated with neat DIAD (150 μL, 0.771 mmol) and the mixture stirred at the same temperature for 30 min and then at room temperature in the dark for 16 h, concentrated and purified in a cromatographic cartridge of silicagel (24 g) eluted with 10% to 40% EtOAc in hexane, to get 143 mg (83%) of the title compound as white foam MS: m/z=955.3 (MH+).

Workup

  1. waitat room temperature in the dark for 16 h
  2. concentrationconcentrated
  3. custompurified in a cromatographic cartridge of silicagel (24 g)
  4. washeluted with 10% to 40% EtOAc in hexane

Sources & evidence

ORD record
ord-864f13b25010429c800579de744beb2e
Source dataset
uspto-grants-2015_11
Patent number
US09187415B2

Reaction notes

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