Hydrochloric Acid → HCID 66833518, compound

HRID 579498Notes

Reaction equation

HRID 579498 reaction equation
N1CCC(CO)CC1.C([O:11][C:12](=[O:45])[C@:13]([NH:37]C(OC(C)(C)C)=O)([CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][CH:32]([CH2:35][OH:36])[CH2:31][CH2:30]1)[CH2:14][CH2:15][CH2:16][CH2:17][B:18]1[O:22]C(C)(C)C(C)(C)[O:19]1)C.[ClH:46]>O>[ClH:46].[ClH:46].[NH2:37][C:13]([CH2:27][CH2:28][N:29]1[CH2:30][CH2:31][CH:32]([CH2:35][OH:36])[CH2:33][CH2:34]1)([CH2:14][CH2:15][CH2:16][CH2:17][B:18]([OH:22])[OH:19])[C:12]([OH:45])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4207714-PiperidinemethanolHCID 66833515HCID 66833515, compound

Product 1

HCID 66833518HCID 66833518, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(2-Amino-6-borono-2-[2-(4-hyrdoxymethylpiperidin-1-yl)-ethyl]-hexanoic acid dihydrochloride is prepared in a manner analogous to that set forth in Example 16, except piperidin-4-ylmethanol is used as the amine in step 6. The final step is as follows: a solution of (R)-2-tert-butoxycarbonylamino-2-[2-(4-hydroxymethyl-piperidin-1-yl)-ethyl]-6-(4,4,5,5-tetramethyl-[1,3,2]-dioxa-borolan-2-yl)-hexanoic acid ethyl ester (78 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 (20 mg, 53%); 1H NMR (D2O, 300 MHz) δ 3.48 (m, 2H), 3.33 (d, J=6 Hz, 2H), 3.21 (m, 1H), 3.04 (m, 1H), 2.86 (m, 2H), 2.19 (2H, t, J=8.5 Hz), 1.86 (m, 2H), 1.60-1.78 (m, 3H), 1.20-1.36 (m, 5H), 1.09 (m, 1H) and 0.64 (t, J=7.5 Hz, 2H,); MS (+CI): m/z for C12H25BN2O4: expected 272.2. found 273.2 (M+H)+.

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-5f4a620fcc544ce1b6a37cf32d484c5c
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

Loading…