Hydrochloric Acid → HCID 66833601, compound

HRID 579550Notes

Reaction equation

HRID 579550 reaction equation
C(O[C:6]([N:8](C)[C:9]([CH2:30][CH2:31][CH2:32][N:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)([CH2:17][CH2:18][CH2:19][CH2:20][B:21]1[O:25]C(C)(C)C(C)(C)[O:22]1)[C:10]([O:12]C(C)(C)C)=[O:11])=O)(C)(C)C.[ClH:39]>O>[ClH:39].[ClH:39].[B:21]([CH2:20][CH2:19][CH2:18][CH2:17][C:9]([NH:8][CH3:6])([CH2:30][CH2:31][CH2:32][N:33]1[CH2:34][CH2:35][CH2:36][CH2:37]1)[C:10]([OH:12])=[O:11])([OH:22])[OH:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66832625HCID 66832625, compound

Product 1

HCID 66833601HCID 66833601, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of tert-butyl 2-(tert-butoxycarbonyl(methyl)amino)-2-(3-(pyrrolidin-1-yl)propyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate (183 mg, 0.33 mmol) in 6 N hydrochloric acid (5 mL) was stirred at 95° C. overnight. After cooling to room temperature, the reaction mixture was transferred to a separatory funnel, diluted with deionized water (5 mL) and washed with dichloromethane (3×). The aqueous layer was frozen in liquid nitrogen and lyophilized to give 6-borono-2-(methylamino)-2-(3-(pyrrolidin-1-yl)propyl)hexanoic acid dihydrochloride, as a colorless foam (81 mg, 80%). 1H NMR (D2O, 300 MHz) δ 3.55-3.45 (m, 2H), 3.14-3.05 (m, 2H), 2.98-2.87 (m, 2H), 2.53 (s, 3H), 2.03-1.92 (m, 2H), 1.92-1.76 (m, 6H), 1.76-1.64 (m, 1H), 1.62-1.48 (m, 1H), 1.36-1.14 (m, 3H), 1.14-0.98 (m, 1H), 0.64 (t, J=7.2 Hz, 2H). ESI MS found for C14H29BN2O4 m/z [301.2 (M+1)].

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-9bd3e719e8a84a5fa4e07dcc608c9f5e
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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