Triphenylphosphine → HCID 54193464, compound

HRID 850679Notes

Reaction equation

HRID 850679 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([CH2:55][CH2:56]O)[CH2:54][CH2:53][O:52][CH2:51][CH2:50]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]([CH2:56][CH2:55][N:49]3[CH2:54][CH2:53][O:52][CH2:51][CH2:50]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 611632-MorpholinoethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 54478802HCID 54478802, compound

Product 1

HCID 54193464HCID 54193464, compoundYield 155.3%

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 (52.5 mg in 1.6 mL dry benzene) was added 20.3 mg 2-morpholin-4-yl-ethanol followed by 40.8 mg triphenylphosphine and 0.025 mL of diethyl azodicarboxylate added dropwise. After 20 minutes, the mixture was concentrated and the crude reaction product purified by flash chromatography on silica gel (ethyl acetate:hexane, 1:3) to give the title compound (95.2 mg).

Workup

  1. additionadded dropwise
  2. concentrationthe mixture was concentrated
  3. customthe crude reaction product
  4. custompurified by flash chromatography on silica gel (ethyl acetate:hexane, 1:3)

Sources & evidence

ORD record
ord-02a6a88c4496464a8804d9bc622d899d
Source dataset
uspto-grants-2000_01
Patent number
US06017944

Reaction notes

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