Hydrochloric Acid → HCID 66833399, compound

HRID 579500Notes

Reaction equation

HRID 579500 reaction equation
C(C1CCNCC1)C1C=CC=CC=1.C([O:16][C:17](=[O:55])[C:18]([CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][CH:45]([CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:44][CH2:43]1)([NH:32]C(OC(C)(C)C)=O)[CH2:19][CH2:20][CH2:21][CH2:22][B:23]1[O:27]C(C)(C)C(C)(C)[O:24]1)C.[ClH:56]>O>[ClH:56].[ClH:56].[NH2:32][C:18]([CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][CH:45]([CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:44][CH2:43]1)([CH2:19][CH2:20][CH2:21][CH2:22][B:23]([OH:27])[OH:24])[C:17]([OH:55])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 317384-BenzylpiperidineHCID 66832784HCID 66832784, compound

Product 1

HCID 66833399HCID 66833399, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-2-[2-(4-benzylpiperidin-1-yl)ethyl]-6-borono-hexanoic acid dihydrochloride is prepared in a manner analogous to that set forth in Example 16, except 4-benzylpiperidine is used as the amine in step 6. The final step is as follows: a solution of 2-[2-(4-benzylpiperidin-1-yl)ethyl]-2-tert-butoxycarbonylamino-6-(4,4,5,5-tetramethyl-[1,3,2]-dioxa-borolan-2-yl)-hexanoic acid ethyl ester (95 mg) 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 the title compound as a colorless foam (42 mg); 1H NMR (D2O, 300 MHz) δ 7.24 (m, 2H), 7.13 (m, 3H), 3.42 (m, 2H), 3.18 (m, 1H), 3.00 (m, 1H), 2.78 (m, 2H), 2.44 (d, J=7.0 Hz, 2H), 2.16 (t, J=7.0 Hz, 2H), 1.76 (m, 5H), 1.24 (m, 5H), 1.09 (m, 1H) and 0.61 (t, J=7.0 Hz, 2H); MS (+CI): m/z for C20H33BN2O4: expected 376.3. found 377.2 (M+H)+, 359.2 (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-4cca77494ba24bfa99b1e5493ca554fe
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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