HCID 66833598, compound → HCID 66833576, compound

HRID 579554Notes

Reaction equation

HRID 579554 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][NH:7][CH:8]([CH2:14][CH2:15][CH2:16][CH2:17][B:18]2[O:22]C(C)(C)C(C)(C)[O:19]2)[C:9]([O:11]CC)=[O:10])=[CH:4][CH:3]=1>Cl>[ClH:1].[B:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH:8]([NH:7][CH2:6][C:5]1[CH:27]=[CH:28][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:9]([OH:11])=[O:10])([OH:19])[OH:22]

Participants

3

Reactant 1

HCID 66833598HCID 66833598, compound

Product 1

HCID 66833576HCID 66833576, compoundYield 148.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of ethyl 2-(4-chlorobenzylamino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate (59 mg) in aq 6 M HCl was heated to reflux for 16 h, concentrated to dryness and purified by preparative HPLC. The residue was redissolved in 2 N HCl and evaporated to give 6-borono-2-(4-chlorobenzylamino)hexanoic acid hydrochloride (36 mg, 83%). 1H NMR (CD3OD, 300 MHz) δ 7.56-7.46 (m, 4H), 4.23 (s, 2H), 4.09-3.98 (m, 1H), 2.02-1.91 (m, 2H), 1.52-1.37 (m, 4H), 0.81 (t, J=7.0 Hz, 2H). ESI MS found for C13H19B1Cl1N1O4 m/z [300.2 (M+1)].

Workup

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

Sources & evidence

ORD record
ord-ed2e17797d6149cc8c4a758a87613de6
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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