Ammonia → N2-methyl-N-[3-(triphenylphosphonio)propyl]glycinamide chloride

HRID 58335Notes

Reaction equation

HRID 58335 reaction equation
C(O[C:6]([N:8](C)[CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][P+:16]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([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)=[O:11])=O)(C)(C)C.[Cl-:36].Cl.C(OCC)C.N>C(Cl)Cl.CO>[CH3:6][NH:8][CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][P+:16]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:11].[Cl-:36]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 131737005N2-(tert-butoxycarbonyl)-N2-methyl-N-[3-(triphenylphosphonio)propyl]glycinamide chloride

Product 1

HCID 131737006N2-methyl-N-[3-(triphenylphosphonio)propyl]glycinamide chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of N2-(tert-butoxycarbonyl)-N2-methyl-N-[3-(triphenylphosphonio)propyl]glycinamide chloride (7.6 g, 14 mol) in methylene chloride (38 mL) and methanol (4.2 mL) was added 2.0 M HCl in diethyl ether (16 mL, 32 mmol), and the mixture was stirred overnight at room temperature. The solution was cooled to 0° C. and treated with 7 M ammonia in methanol (6.0 mL, 42 mmol), giving an immediate white precipitate. After 30 minutes, the slurry was filtered and the flask and filter cake were rinsed with methylene chloride (68 mL). The filtrate was concentrated to give the title compound (6.2 g, 100%) as a crude white solid.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. customgiving an immediate white precipitate
  3. waitAfter 30 minutes
  4. filtrationthe slurry was filtered
  5. filtrationthe flask and filter cake
  6. washwere rinsed with methylene chloride (68 mL)
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-dd5c36bf369e4300a33843e92a619a23
Source dataset
uspto-grants-2016_09
Patent number
US09434753B2

Reaction notes

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