Tert-Butyl hypochlorite → HCID 45267158, compound

HRID 2061032Notes

Reaction equation

HRID 2061032 reaction equation
[ClH:1].[NH2:2][C:3]([CH3:16])([CH3:15])[CH2:4][C:5]([N:7]([CH2:9][CH2:10][N+:11]([CH3:14])([CH3:13])[CH3:12])[CH3:8])=[O:6].C(O[Cl:22])(C)(C)C>CO>[Cl-:22].[Cl:1][N:2]([Cl:22])[C:3]([CH3:16])([CH3:15])[CH2:4][C:5]([N:7]([CH2:9][CH2:10][N+:11]([CH3:12])([CH3:14])[CH3:13])[CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 86642698HCID 86642698, compound

Product 1

HCID 45267158HCID 45267158, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(3-amino-N,3-dimethylbutanamido)-N,N,N-trimethylethanaminium hydrochloride (511 mg, 2.0 mmol) in methanol (40 ml) was added tert-butylhypochlorite (0.77 g, 7.1 mmol). The mixture was stirred for 1 hour at room temperature. The reaction mixture was concentrated in vacuo, and purified by prep-HPLC to give 253 mg (39%) of 2-(3-(dichloroamino)-N,3-dimethylbutanamido)-N,N,N-trimethylethanaminium chloride. 1H NMR (D2O) δ 3.88 (t, J=5.4 Hz, 2 H), 3.53 (t, J=5.4, 2 H), 3.26 (s, 3 H), 3.21 (s, 9 H), 2.98 (s, 2 H), 1.51 (s, 6 H); calc. for C11H24C12N3O+: 284.13, Found: 284.1 (M+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-ad394e7c10f34852a980ff0b143ba659
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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