Hydrochloric Acid → HCID 66832924, compound

HRID 579499Notes

Reaction equation

HRID 579499 reaction equation
C(N(CC)C(C1CCCNC1)=O)C.C([O:16][C:17](=[O:55])[C:18]([NH:47]C(OC(C)(C)C)=O)([CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][CH2:37][CH:36]([C:40](=[O:46])[N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH2:35]1)[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].[NH2:47][C:18]([CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][CH2:37][CH:36]([C:40](=[O:46])[N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH2:35]1)([CH2:19][CH2:20][CH2:21][CH2:22][B:23]([OH:24])[OH:27])[C:17]([OH:55])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18793N,N-Diethylpiperidine-3-carboxamideHCID 86663715HCID 86663715, compound

Product 1

HCID 66832924HCID 66832924, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-6-borono-2-[2-(3-diethylcarbamoyl-piperidin-1-yl)-ethyl]-hexanoic acid dihydrochloride is prepared in a manner analogous to that set forth in Example 16, except N,N-diethylpiperidine-3-carboxamide is used as the amine in step 6. The final step is as follows: a solution of (2R/S, 3″R/S)-2-tert-butoxycarbonylamino-2-[2-(3-diethylcarbamoyl-piperidin-1-yl)-ethyl]-6-(4,4,5,5-tetramethyl-[1,3,2]-dioxa-borolan-2-yl)-hexanoic acid ethyl ester (128 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 a diastereomeric mixture of the title compounds as a colorless foam (54 mg); 1H NMR (D2O, 300 MHz) δ 3.46 (m, 2H), 3.26 (m, 4H), 3.10 (m, 2H), 2.94 (m, 4H), 2.20 (m, 2H), 1.62-1.92 (6H, m), 1.28 (m, 2H), 1.10 (t, J=7.0 Hz, 3H), 1.06 (m, 1H), 0.93 (t, J=7.0 Hz, 3H) and 0.64 (t, J=7.5 Hz, 2H); MS (+CI): m/z for C18H36BN3O5: expected 385.3. found 386.2 (M+H)+, 368.2 (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
  4. customto give

Sources & evidence

ORD record
ord-75b895702aac4482815b9b4f6e33ab43
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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