Triphenylphosphine → HCID 53972788, compound

HRID 1603068Notes

Reaction equation

HRID 1603068 reaction equation
[CH:1]12[N:7]([C:8](=[O:48])[C:9]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[NH:17][C:16]([C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[CH:22]=3)=[C:15]4[C@H:29]([CH3:47])[CH2:30][NH:31][S:32]([C:35]3[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][C:36]=3[N+:44]([O-:46])=[O:45])(=[O:34])=[O:33])([CH3:11])[CH3:10])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[N:49]1[N:50]=[CH:51][N:52]([C:54]2[CH:59]=[CH:58][C:57]([CH2:60][CH2:61]O)=[CH:56][CH:55]=2)[CH:53]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>>[CH:4]12[N:7]([C:8](=[O:48])[C:9]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[NH:17][C:16]([C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[CH:22]=3)=[C:15]4[C@H:29]([CH3:47])[CH2:30][N:31]([CH2:61][CH2:60][C:57]3[CH:56]=[CH:55][C:54]([N:52]4[CH:53]=[N:49][N:50]=[CH:51]4)=[CH:59][CH:58]=3)[S:32]([C:35]3[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][C:36]=3[N+:44]([O-:46])=[O:45])(=[O:33])=[O:34])([CH3:10])[CH3:11])[CH:1]([CH2:2][CH2:3]1)[CH2:6][CH2:5]2

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19608677HCID 19608677, compoundHCID 54478802HCID 54478802, compound

Product 1

HCID 53972788HCID 53972788, compoundYield 99.6%

Procedure

To a solution of (S)-N-{2-[5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl 2-oxo-ethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-propyl}-2,4-dinitrobenzenesulfonamide (0.197 g in 6 mL dry benzene:N,N-dimethylformamide, 2:1) was added 0.083 g 2-(4-[1,2,4]triazol-4-yl-phenyl)ethanol followed by 0.115 g triphenylphosphine and 0.069 mL of diethyl azodicarboxylate added dropwise. After 1.5 hours, the mixture was concentrated and the crude reaction product purified by flash chromatography on silica gel (methylene chloride:methanol, 95:5) to give the title compound (0.246 g).

Workup

  1. additionadded dropwise
  2. concentrationthe mixture was concentrated
  3. customthe crude reaction product
  4. custompurified by flash chromatography on silica gel (methylene chloride:methanol, 95:5)

Sources & evidence

ORD record
ord-35eb2f4c359a4185ac48b5b88c9cf8ad
Source dataset
uspto-grants-1999_11
Patent number
US05985901

Reaction notes

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