Sodium Azide → HCID 86610010, compound

HRID 1176503Notes

Reaction equation

HRID 1176503 reaction equation
[F:1][C:2]1[CH:60]=[CH:59][C:58]([F:61])=[CH:57][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])[CH2:17][CH:16]2[O:31][CH2:32][C:33]2[CH:34]=[CH:35][C:36]3[O:41][CH2:40][C:39](=[O:42])[N:38]([CH2:43][CH2:44]OS(C4C=CC(C)=CC=4)(=O)=O)[C:37]=3[CH:56]=2)=[CH:11][CH:10]=1.[N-:62]=[N+:63]=[N-:64].[Na+]>CN(C)C=O>[N:62]([CH2:44][CH2:43][N:38]1[C:37]2[CH:56]=[C:33]([CH2:32][O:31][CH:16]3[CH:15]([C:12]4[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][CH2:5][O:4][C:3]5[CH:57]=[C:58]([F:61])[CH:59]=[CH:60][C:2]=5[F:1])=[CH:10][CH:11]=4)[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[O:22])[CH2:17]3)[CH:34]=[CH:35][C:36]=2[O:41][CH2:40][C:39]1=[O:42])=[N+:63]=[N-:64]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86610011HCID 86610011, compound

Product 1

HCID 86610010HCID 86610010, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.880 g of benzyl 4-{4-[3-(2,5-difluorophenoxy)propoxy]phenyl}-3-{3-oxo-4-[2-(toluene-4-sulphonyloxy)ethyl]-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy}piperidine-1-carboxylate and 0.532 g of sodium azide in 10 ml of N,N-dimethylformamide is stirred at 65° C. over 90 minutes. The reaction mixture is poured onto water (40 ml) and extracted with tert-butyl methyl ether (2×40 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=0.11 (1:2 EtOAc-heptane). Rt=5.82

Workup

  1. additionThe reaction mixture is poured onto water (40 ml)
  2. extractionextracted with tert-butyl methyl ether (2×40 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-17948cf784224f1186471fd62d2fa9a4
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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