Tert-butyl 2-(2-(4-chlorophenoxy)ethyl)-2-(diphenylmethyleneamino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate → 2-Amino-6-borono-2-(2-(4-chlorophenoxy)ethyl)hexanoic acid hydrochloride

HRID 579520Notes

Reaction equation

HRID 579520 reaction equation
C([O:5][C:6](=[O:45])[C:7]([N:31]=C(C1C=CC=CC=1)C1C=CC=CC=1)([CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[CH2:8][CH2:9][CH2:10][CH2:11][B:12]1[O:16]C(C)(C)C(C)(C)[O:13]1)(C)(C)C>Cl.O>[ClH:30].[NH2:31][C:7]([CH2:21][CH2:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=1)([CH2:8][CH2:9][CH2:10][CH2:11][B:12]([OH:13])[OH:16])[C:6]([OH:45])=[O:5]

Participants

4

Reactant 1

HCID 86663721Tert-butyl 2-(2-(4-chlorophenoxy)ethyl)-2-(diphenylmethyleneamino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate

Product 1

HCID 668325062-Amino-6-borono-2-(2-(4-chlorophenoxy)ethyl)hexanoic acid hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 2-(benzhydrylidene-amino)-2-[2-(4-chlorophenoxy)-ethyl]-6-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-hexanoic acid tert-butyl ester (486 mg) in 6 N HCl (6 ml) was warmed to 60° C. and stirred overnight. After cooling to room temperature, the reaction mixture was transferred to a separatory funnel, diluted with deionized water (6 ml) and washed with dichloromethane (3×). The aqueous layer was frozen in liquid nitrogen and lyophilized to give 2-amino-6-borono-2-(2-(4-chlorophenoxy)ethyl)hexanoic acid hydrochloride, as a colorless foam (125 mg, 85%); 1H NMR (D4-MeOH, 300 MHz) δH 7.24 (2H, d, J=7 Hz, 2H), 6.94 (d, J=7 Hz, 2H), 4.18 (m, 2H), 2.52 (m, 1H), 2.46 (m, 1H), 1.92 (m, 2H), 1.22-1.52 (m, 4H) and 0.82 (t, J=7 Hz, 2H,); MS (+CI): m/z for C14H21BClNO5: expected 329.1. found 330.2 (M+H)+, 312.2 (M+H−H2O)+, 659.4 (2 M+H)+, 641.4 (2 M+H−H2O)+.

Workup

  1. customthe reaction mixture was transferred to a separatory funnel
  2. washwashed with dichloromethane (3×)
  3. temperatureThe aqueous layer was frozen in liquid nitrogen

Sources & evidence

ORD record
ord-491e3520c10848bab667da8d69db74d2
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

Loading…