Hydrochloric Acid → HCID 66833333, compound

HRID 579497Notes

Reaction equation

HRID 579497 reaction equation
C(NCCO)C1C=CC=CC=1.C([O:14][C:15](=[O:51])[C:16]([CH2:38][CH2:39][N:40]([CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:41][CH2:42][OH:43])([NH:30]C(OC(C)(C)C)=O)[CH2:17][CH2:18][CH2:19][CH2:20][B:21]1[O:25]C(C)(C)C(C)(C)[O:22]1)C.[ClH:52]>O>[ClH:52].[ClH:52].[NH2:30][C:16]([CH2:38][CH2:39][N:40]([CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:41][CH2:42][OH:43])([CH2:17][CH2:18][CH2:19][CH2:20][B:21]([OH:22])[OH:25])[C:15]([OH:51])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4348BenzylethanolamineHCID 131732890HCID 131732890, compound

Product 1

HCID 66833333HCID 66833333, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-2-{2-[benzyl-(2-hydroxyethyl)-amino]-ethyl}-6-borono-hexanoic acid dihydrochloride is prepared in a manner analogous to that set forth in Example 16, except 2-(benzylamino)ethanol is used as the amine in step 6. The final step is as follows: a solution of 2-{2-[benzyl-(2-hyrdoxyethyl)-amino]-ethyl}-2-tert-butoxycarbonylamino-6-(4,4,5,5-tetramethyl-[1,3,2]-dioxa-borolan-2-yl)-hexanoic acid ethyl ester (111 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 colorless foam (48 mg); 1H NMR (D2O, 300 MHz) δ 7.35 (s, 5H), 4.11-4.25 (m, 2H), 3.76 (s, 2H), 3.06-3.34 (m, 4H), 2.18 (m, 2H), 1.76 (m, 1H), 1.43 (m, 1H), 1.18 (m, 4H) and 0.56 (m, 2H); MS (+CI): m/z for C17H29BN2O5: expected 352.2. found 371.2 (M+H+H2O)+353.2 (M+H)+, 335.2 (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-9a8826f8a43042c8956946de8216755e
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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