Ammonia → (4-{[2,2-Dimethyl-4-(methylamino)butanoyl]amino}butyl) (triphenyl)phosphonium bromide

HRID 58344Notes

Reaction equation

HRID 58344 reaction equation
[Br-:1].[CH3:2][C:3]([CH3:41])([CH2:30][CH2:31][N:32](C)[C:33](=O)OC(C)(C)C)[C:4](=[O:29])[NH:5][CH2:6][CH2:7][CH2:8][CH2:9][P+:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.C(OCC)C.N>C(Cl)Cl.CO>[Br-:1].[CH3:2][C:3]([CH3:41])([CH2:30][CH2:31][NH:32][CH3:33])[C:4]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][P+:10]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:29]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 894633688,8,11,14,14-Pentamethyl-7,12-dioxo-1,1,1-triphenyl-13-oxa-6,11-diaza-1-phosphoniapentadecane bromide

Product 1

HCID 89463386(4-{[2,2-Dimethyl-4-(methylamino)butanoyl]amino}butyl) (triphenyl)phosphonium bromideYield 98.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

8,8,11,14,14-pentamethyl-7,12-dioxo-1,1,1-triphenyl-13-oxa-6,11-diaza-1-phosphoniapentadecane bromide (205 mg, 0.32 mmol) was dissolved in methylene chloride (1.0 mL) and methanol (0.10 mL). The solution at room temperature was treated with 2.0 M hydrogen chloride in diethyl ether (0.36 mL, 0.71 mmol). The reaction was stirred overnight at room temperature, cooled with an ice bath, and treated with 7N ammonia in methanol (0.13 mL, 0.93 mmol). After 30 minutes, the slurry that resulted was filtered, and the solids were washed with methylene chloride. The filtrate was concentrated to give the title compound (170 mg, 98%) as a white foam. The product of step 2 was used crude in next step.

Workup

  1. temperaturecooled with an ice bath
  2. waitAfter 30 minutes
  3. customthe slurry that resulted
  4. filtrationwas filtered
  5. washthe solids were washed with methylene chloride
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-881f328a1340427996a43394277a39bc
Source dataset
uspto-grants-2016_09
Patent number
US09434753B2

Reaction notes

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