Lithium Chloride → N2-(tert-butoxycarbonyl)-N2-methyl-N-[3-(triphenylphosphonio)propyl]glycinamide chloride

HRID 58334Notes

Reaction equation

HRID 58334 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:35])[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:7])([CH3:4])([CH3:3])[CH3:2].[Br-].[Cl-:37].[Li+]>C(Cl)Cl.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6]([N:8]([CH3:35])[CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][P+:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([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)=[O:11])=[O:7])([CH3:3])([CH3:4])[CH3:2].[Cl-:37]

Participants

5

Reactant 2

HCID 433294Lithium ChlorideHCID 131737003HCID 131737003, compound

Product 1

HCID 131737005N2-(tert-butoxycarbonyl)-N2-methyl-N-[3-(triphenylphosphonio)propyl]glycinamide chloride

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of N2-(tert-butoxycarbonyl)-N2-methyl-N-[3-(triphenylphosphonio)propyl]glycinamide bromide (53.7 g, 93.9 mmole) in methylene chloride (450 mL) was stirred with 20 weight percent aqueous lithium chloride containing 2 weight percent tetrabutylammonium chloride (4×150 mL/g). The organic layer was concentrated to dryness give the title compound in quantitative yield.

Workup

  1. concentrationThe organic layer was concentrated to dryness

Sources & evidence

ORD record
ord-b3621d7d8476470a9c265f26cb6cbc17
Source dataset
uspto-grants-2016_09
Patent number
US09434753B2

Reaction notes

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