Hydrochloric Acid → HCID 66833498, compound

HRID 579494Notes

Reaction equation

HRID 579494 reaction equation
C([O:3][C:4](=[O:41])[C:5]([NH:33]C(OC(C)(C)C)=O)([CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[N:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH2:23][CH2:22]1)[CH2:6][CH2:7][CH2:8][CH2:9][B:10]1[O:14]C(C)(C)C(C)(C)[O:11]1)C.[ClH:42]>O>[ClH:42].[ClH:42].[ClH:42].[NH2:33][C:5]([CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][N:24]([C:27]2[N:28]=[CH:29][CH:30]=[CH:31][N:32]=2)[CH2:25][CH2:26]1)([CH2:6][CH2:7][CH2:8][CH2:9][B:10]([OH:11])[OH:14])[C:4]([OH:41])=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131732887HCID 131732887, compound

Product 1

HCID 66833498HCID 66833498, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-6-borono-2-[2-(4-pyrimidin-2-yl-piperazin-1-yl)ethyl]-hexanoic acid trihydrochloride is prepared in a manner analogous to that set forth in Example 16, except 1-2-(1-piperidinyl)pyrimidine is used as the amine in step 6. The final step is as follows: a solution of (R/S)-2-tert-butoxycarbonylamino-2-[2-(4-pyrimidin-2-yl-piperazin-1-yl)-ethyl]-6-(4,4,5,5-tetramethyl-[1,3,2]-dioxa-borolan-2-yl)-hexanoic acid ethyl ester (126 mg) in 6 N hydrochloric acid (6 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 the title compound as a white solid (80 mg, 83%); 1H NMR (D2O, 300 MHz) δ 8.47 (d, J=5.5 Hz, 2H), 6.96 (t, J=5.5 Hz, 1H), 3.48-3.76 (m, 4H), 3.14-3.40 (m, 6H), 2.29 (t, J=8 Hz, 2H), 1.81 (m, 2H), 1.28 (m, 3H), 1.11 (m, 1H) and 0.62 (t, J=7.5 Hz, 2H).

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-4b17c5ea087f4364aff0160f98bbe12c
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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