Ammonia → (4-{[4-(Methylamino)butanoyl]amino}butyl)(triphenyl)phosphonium bromide
Reaction equation
[Br-:1].[CH3:2][N:3](C(=O)OC(C)(C)C)[CH2:4][CH2:5][CH2:6][C:7](=[O:32])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][P+:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.C(OCC)C.N>C(Cl)Cl.CO>[Br-:1].[CH3:2][NH:3][CH2:4][CH2:5][CH2:6][C:7]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][P+:13]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:32]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
11,14,14-trimethyl-7,12-dioxo-1,1,1-triphenyl-13-oxa-6,11-diaza-1-phosphoniapentadecane bromide (910 mg, 1.50 mmol) was dissolved in methylene chloride (4.6 mL) and methanol (0.50 mL). The solution at room temperature was treated with 2.0 M hydrogen chloride in diethyl ether (1.63 mL, 3.26 mmol). The mixture was stirred overnight at room temperature, then cooled with an ice bath and treated with 7N ammonia in methanol (0.61 mL, 4.30 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 (690 mg, 91%, 91% pure) as a white foam. The product of step 2 was used crude in next step.
Workup
- temperaturecooled with an ice bath
- waitAfter 30 minutes
- customthe slurry that resulted
- filtrationwas filtered
- washthe solids were washed with methylene chloride
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-0cfcf14d2fc74acc94f03bcc30aa4eb3
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434753B2
Reaction notes
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