HCID 66833759, compound → HCID 86663731, compound

HRID 579556Notes

Reaction equation

HRID 579556 reaction equation
C(O[C:6]([N:8](C)[CH:9]([CH2:15][CH2:16][CH2:17][CH2:18][B:19]1[O:23]C(C)(C)C(C)(C)[O:20]1)[C:10]([O:12]CC)=[O:11])=O)(C)(C)C>Cl>[B:19]([CH2:18][CH2:17][CH2:16][CH2:15][CH:9]([NH:8][CH3:6])[C:10]([OH:12])=[O:11])([OH:23])[OH:20]

Participants

3

Reactant 1

HCID 66833759HCID 66833759, compound

Product 1

HCID 86663731HCID 86663731, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of ethyl 2-(tert-butoxycarbonyl(methyl)amino)-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-(methylamino)hexanoic acid as a white solid (24 mg, 72%). 1H NMR (CD3OD, 300 MHz) δ 3.94 (t, J=5.9 Hz), 2.72 (s, 3H), 1.45-1.34 (m, 4H), 0.81 (t, J=7.0 Hz, 2H). ESI MS found for C7H16B1N1O4 m/z [190.0 (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-0e5c9610795d4c29afbd3e9a3eb4cfed
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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