Triphenylphosphine → HCID 58790022, compound

HRID 418645Notes

Reaction equation

HRID 418645 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[F:13][C:14]1[CH:38]=[C:37]([N+:39]([O-:41])=[O:40])[CH:36]=[CH:35][C:15]=1[O:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19]2[CH:23]=[C:24]([C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([O:33][CH3:34])[CH:27]=3)[S:25][C:18]=12.[O:42]1[CH2:47][CH2:46][N:45]([CH2:48][CH2:49]O)[CH2:44][CH2:43]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:13][C:14]1[CH:38]=[C:37]([N+:39]([O-:41])=[O:40])[CH:36]=[CH:35][C:15]=1[O:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19]2[CH:23]=[C:24]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:49][CH2:48][N:45]4[CH2:46][CH2:47][O:42][CH2:43][CH2:44]4)=[C:28]([O:33][CH3:34])[CH:27]=3)[S:25][C:18]=12

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 5462977Diethyl azodicarboxylateHCID 136019957HCID 136019957, compound

Product 1

HCID 58790022HCID 58790022, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DEAD (0.96 mL, 6.07 mmol) was added to a solution of the compound 137 (1.78 g, 4.33 mmol), 2-morpholinoethanol (0.74 mL, 6.07 mmol) and triphenylphosphine (1.59 g, 6.07 mmol) in THF (43 mL). The reaction mixture was stirred at room temperature until completion of the reaction. The mixture was quenched with a saturated aqueous solution of ammonium chloride then extracted three times with ethyl acetate and 3 times with dichloromethane (with a bit of methanol inside). The combined organic layers were washed with water and brine, dried over anhydrous MgSO4, filtered and evaporated. The residue was triturated with diethyl ether, filtered and dried on a vacuum pump to afford title compound 138 as a yellow-brown solid (1.80 g, 79% yield). MS (m/z): 526.2 (M+H).

Workup

  1. customThe mixture was quenched with a saturated aqueous solution of ammonium chloride
  2. extractionthen extracted three times with ethyl acetate and 3 times with dichloromethane (with a bit of methanol inside)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was triturated with diethyl ether
  8. filtrationfiltered
  9. customdried on a vacuum pump

Sources & evidence

ORD record
ord-c51853fe18cb496ba0ad115dc16c341b
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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