Methanol → HCID 86616089, compound

HRID 2353990Notes

Reaction equation

HRID 2353990 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:6][CH2:7][C:8]([NH:10][CH:11]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]2[NH:22][N:21]=[N:20][N:19]=2)[C:13]2[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:12]1=2)=[O:9].[C:37]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.CO>C(Cl)Cl.O>[F:36][C:2]([F:1])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:32])([F:34])[F:33])[CH:30]=1)[CH2:6][CH2:7][C:8]([NH:10][CH:11]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]2[N:19]=[N:20][N:21]([CH3:37])[N:22]=2)[C:13]2[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:12]1=2)=[O:9]

Participants

7

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 178520473HCID 178520473, compound

Product 1

HCID 86616089HCID 86616089, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3,5-Bis-trifluoromethyl-benzyl-N-[8-chloro-1-(1H-tetrazol-5-yl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl]-acetamide (0.55 mmol, 0.29 g) in CH2Cl2 (5 mL) was added triphenyl phosphine (0.55 mmol, 0.14 g) and diethylazo dicarboxylate (0.55 mmol, 90.0 μL) at 0° C. To the above mixture, MeOH (2.75 mmol, 0.11 μL) was added and warmed to room temperature for 48 h. After completion, the reaction mixture was diluted with water (20 mL), extracted with EtOAC (3×25 mL) and the combined organic layers were washed with water and brine. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude compound was purified by flash column chromatography to afford the title compound as colorless foam; Rf 0.60 (EtOAc-Hexane, 1:1, v/v); MS (ES+): 547 (M+H+).

Workup

  1. extractionextracted with EtOAC (3×25 mL)
  2. washthe combined organic layers were washed with water and brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude compound was purified by flash column chromatography

Sources & evidence

ORD record
ord-bd98cf050a6f46fd8a9bc4834cd1690f
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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