Ammonia → HCID 68497803, compound

HRID 1176502Notes

Reaction equation

HRID 1176502 reaction equation
[N:1]([CH2:4][CH2:5][N:6]1[C:11]2[CH:12]=[C:13]([CH2:16][O:17][CH:18]3[CH:23]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33][O:34][C:35]5[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=5[F:42])=[CH:26][CH:25]=4)[CH2:22][CH2:21][N:20]([C:43]([O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)=[O:44])[CH2:19]3)[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][C:7]1=[O:53])=[N+]=[N-].N.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O.CO>[NH2:1][CH2:4][CH2:5][N:6]1[C:11]2[CH:12]=[C:13]([CH2:16][O:17][CH:18]3[CH:23]([C:24]4[CH:25]=[CH:26][C:27]([O:30][CH2:31][CH2:32][CH2:33][O:34][C:35]5[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=5[F:42])=[CH:28][CH:29]=4)[CH2:22][CH2:21][N:20]([C:43]([O:45][CH2:46][C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)=[O:44])[CH2:19]3)[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][C:7]1=[O:53]

Participants

7

Reactant 3

HCID 222AmmoniaHCID 11776TriphenylphosphineHCID 86610010HCID 86610010, compound

Product 1

HCID 68497803HCID 68497803, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.660 g of benzyl 3-[4-(2-azidoethyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-{4-[3-(2,5-difluorophenoxy)propoxy]phenyl}piperidine-1-carboxylate in 2.5 ml of tetrahydrofuran and 0.55 ml of water is admixed at room temperature with a solution of 0.55 ml of 25% conc. ammonia in 2.4 ml of methanol. After 0.357 g of triphenylphosphine has been added, the reaction mixture is stirred at room temperature over 16 hours. The reaction mixture is poured onto water (40 ml) and extracted with tert-butyl methyl ether (3×40 ml). The organic phases are washed with brine (20 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.31 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=5.01.

Workup

  1. additionThe reaction mixture is poured onto water (40 ml)
  2. extractionextracted with tert-butyl methyl ether (3×40 ml)
  3. washThe organic phases are washed with brine (20 ml)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-f904c52f25724027b43c6ff6e7245476
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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