Triphenylphosphine → HCID 57160875, compound

HRID 1734380Notes

Reaction equation

HRID 1734380 reaction equation
[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:64])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([O:50][CH2:51][CH:52]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[N:53]=[N+]=[N-])[CH:46]([O:62][CH3:63])[CH2:45]2)[CH:7]([CH3:65])[CH:6]([O:66][Si](C(C)(C)C)(C)C)[CH2:5][C:4]1=[O:74])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:64])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([O:50][CH2:51][CH:52]([C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)[NH2:53])[CH:46]([O:62][CH3:63])[CH2:45]2)[CH:7]([CH3:65])[CH:6]([OH:66])[CH2:5][C:4]1=[O:74])[CH3:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 131719454HCID 131719454, compound

Product 1

HCID 57160875HCID 57160875, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the product from Step A (27 mg) in wet benzene (0.5 ml) was added triphenyl phosphine (15 mg) and the reaction heated to 60° C. for 2 hours. The reaction mixture was concentrated, dissolved in THF (200 μl) and treated with hydrogen fluoride/pyridine for 24 hours at room temperature. The reaction was quenched with saturated aqueous sodium bicarbonate solution and extacted into ethyl acetate. The crude material was purified by preparative plate chromatography (20 cm×20 cm, 500 microns) eluting with 90% dichloromethane:10% methanol+1% ammonium hydroxide to give the title compound (9 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in THF (200 μl)
  3. additiontreated with hydrogen fluoride/pyridine for 24 hours at room temperature
  4. customThe reaction was quenched with saturated aqueous sodium bicarbonate solution
  5. customThe crude material was purified by preparative plate chromatography (20 cm×20 cm, 500 microns)
  6. washeluting with 90% dichloromethane

Sources & evidence

ORD record
ord-87148be7d88a44dc8bd031df82663d82
Source dataset
uspto-grants-1996_07
Patent number
US05532248

Reaction notes

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