ethyl 2-(3-(3,4-dichlorobenzylamino)propyl)-2-(N-methylacetamido)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate → 6-Borono-2-(3-(3,4-dichlorobenzylamino)propyl)-2-(methylamino)hexanoic acid dihydrochloride

HRID 579544Notes

Reaction equation

HRID 579544 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][C:36]=1[Cl:37])[CH2:5][NH:6][CH2:7][CH2:8][CH2:9][C:10]([N:29](C)[C:30](=O)C)([CH2:16][CH2:17][CH2:18][CH2:19][B:20]1[O:24]C(C)(C)C(C)(C)[O:21]1)[C:11]([O:13]CC)=[O:12]>Cl>[ClH:1].[ClH:1].[B:20]([CH2:19][CH2:18][CH2:17][CH2:16][C:10]([CH2:9][CH2:8][CH2:7][NH:6][CH2:5][C:4]1[CH:34]=[CH:35][C:36]([Cl:37])=[C:2]([Cl:1])[CH:3]=1)([NH:29][CH3:30])[C:11]([OH:13])=[O:12])([OH:24])[OH:21]

Participants

3

Reactant 1

HCID 66832776ethyl 2-(3-(3,4-dichlorobenzylamino)propyl)-2-(N-methylacetamido)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate

Product 1

HCID 668337196-Borono-2-(3-(3,4-dichlorobenzylamino)propyl)-2-(methylamino)hexanoic acid dihydrochlorideYield 87.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of ethyl 2-(3-(3,4-dichlorobenzylamino)propyl)-2-(N-methylacetamido)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate (76 mg) in aq 6 M HCl was heated to reflux for 16 h, concentrated to dryness and purified by preparative HPLC. The resulting residue was redissolved in 2 N HCl and evaporated to give 6-borono-2-(3-(3,4-dichlorobenzylamino)propyl)-2-(methylamino)hexanoic acid dihydrochloride (19 mg, 12%-3 steps). 1H NMR (D2O, 500 MHz) δ 7.55 (bs, 1H), 7.51 (d, J=7.5 Hz, 1H), 7.28 (d, J=7.5 Hz, 1H), 4.12 (s, 2H), 3.02 (t, J=7.2 Hz, 2H), 2.55 (s, 3H), 1.91-1.68 (m, 5H), 1.60-1.49 (m, 1H), 1.38-1.29 (m, 2H), 1.28-1.19 (m, 1H), 1.14-1.04 (m, 1H), 0.70 (t, J=7.2 Hz, 2H). ESI MS found for C17H27BCl2N2O4 m/z [405.4/407.4 (M+1)].

Workup

  1. temperatureto reflux for 16 h
  2. concentrationconcentrated to dryness
  3. custompurified by preparative HPLC
  4. dissolutionThe resulting residue was redissolved in 2 N HCl
  5. customevaporated

Sources & evidence

ORD record
ord-f9bfbc86ed014706ae0c9d8f51dcf611
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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