Hydrochloric Acid → HCID 66833114, compound

HRID 579496Notes

Reaction equation

HRID 579496 reaction equation
C(NCC1C=CC=CC=1)C.C([O:13][C:14](=[O:49])[C:15]([CH2:37][CH2:38][N:39]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:40][CH3:41])([NH:29]C(OC(C)(C)C)=O)[CH2:16][CH2:17][CH2:18][CH2:19][B:20]1[O:24]C(C)(C)C(C)(C)[O:21]1)C.[ClH:50]>O>[ClH:50].[ClH:50].[NH2:29][C:15]([CH2:37][CH2:38][N:39]([CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[CH2:40][CH3:41])([CH2:16][CH2:17][CH2:18][CH2:19][B:20]([OH:21])[OH:24])[C:14]([OH:49])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 84352N-EthylbenzylamineHCID 131732889HCID 131732889, compound

Product 1

HCID 66833114HCID 66833114, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-2-[2-(benzyl-ethyl-amino)-ethyl]-6-borono-hexanoic acid dihydrochloride is prepared in a manner analogous to that set forth in Example 16, except ethylbenzylamine is used as the amine in step 6. The final step is as follows: a solution of (R/S)-2-[2-(benzyl-ethyl-amino)-ethyl]-2-tert-butoxycarbonylamino-6-(4,4,5,5-tetramethyl-[1,3,2]-dioxa-borolan-2-yl)-hexanoic acid ethyl ester (104 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 (41 mg); 1H NMR (D2O, 300 MHz) δ 7.36 (s, 5H), 4.31 (m, 1H), 4.11 (m, 1H), 2.96-3.29 (m, 4H), 2.10 (m, 2H), 1.68 (m, 1H), 1.43 (t, J=8 Hz, 1H), 1.21 (t, J=6.5 Hz, 3H), 0.89-1.20 (m, 4H),) and 0.59 (m, 2H); MS (+CI): m/z for C17H29BN2O4: expected 336.2. found 337.2 (M+H)+, 319 (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-eb65d4f74ec841a983cd4a2c08f5d9e5
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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