Hydrochloric Acid → 2-Amino-6-borono-2-(1-hydroxy-propyl)-hexanoic acid hydrochloride

HRID 579524Notes

Reaction equation

HRID 579524 reaction equation
C([O:5][C:6]([C:8]1([CH2:27][CH2:28][CH2:29][CH2:30][B:31]2[O:35]C(C)(C)C(C)(C)[O:32]2)[CH:12]([CH2:13][CH3:14])[O:11]C(C2C=CC=CC=2)(C2C=CC=CC=2)[NH:9]1)=[O:7])(C)(C)C.[ClH:40]>O>[ClH:40].[NH2:9][C:8]([CH:12]([OH:11])[CH2:13][CH3:14])([CH2:27][CH2:28][CH2:29][CH2:30][B:31]([OH:35])[OH:32])[C:6]([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 668332165-Ethyl-2,2-diphenyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-butyl]-oxazolidine-4-carboxylic acid tert-butyl ester

Product 1

HCID 866637222-Amino-6-borono-2-(1-hydroxy-propyl)-hexanoic acid hydrochlorideYield 27%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5-ethyl-2,2-diphenyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-butyl]-oxazolidine-4-carboxylic acid tert-butyl ester (152 mg, 0.28 mmol) in 6 N HCl (4 ml) was stirred at 65° C. for 1 day. After cooling to room temperature, the reaction mixture was transferred to a separatory funnel, diluted with deionized water (3 ml) and washed with dichloromethane (3×4 mL). The aqueous layer was frozen in liquid nitrogen and lyophilized to give 2-amino-6-borono-2-(1-hydroxy-propyl)-hexanoic acid hydrochloride as white foam (20 mg, 0.074 mmol, 27%). 1H NMR (D2O, 300 MHz) δ 3.80 (dd, J=11.4, 1.8 Hz, 1H), 1.88-1.50 (m, 2H), 1.48-0.92 (m, 5H), 0.85 (t, J=7.6 Hz, 3H), 0.63 (t, J=7.6 Hz, 2H).

Workup

  1. customthe reaction mixture was transferred to a separatory funnel
  2. washwashed with dichloromethane (3×4 mL)
  3. temperatureThe aqueous layer was frozen in liquid nitrogen

Sources & evidence

ORD record
ord-5e0e3e4d79664c9681dc88d2f261c11c
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

Loading…