Hydrochloric Acid → HCID 87173112, compound

HRID 579495Notes

Reaction equation

HRID 579495 reaction equation
CNCC(O)=O.C([O:9][C:10](=[O:43])[C:11]([NH:35]C(OC(C)(C)C)=O)([CH2:25][CH2:26][N:27]([CH2:29][C:30]([O:32]CC)=[O:31])[CH3:28])[CH2:12][CH2:13][CH2:14][CH2:15][B:16]1[O:20]C(C)(C)C(C)(C)[O:17]1)C.[ClH:44]>O>[ClH:44].[ClH:44].[NH2:35][C:11]([CH2:25][CH2:26][N:27]([CH2:29][C:30]([OH:32])=[O:31])[CH3:28])([CH2:12][CH2:13][CH2:14][CH2:15][B:16]([OH:20])[OH:17])[C:10]([OH:43])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1088SarcosineHCID 131732888HCID 131732888, compound

Product 1

HCID 87173112HCID 87173112, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-6-borono-2-(2-((carboxymethyl)(methyl)amino)ethyl)hexanoic acid dihydrochloride is prepared in a manner analogous to that set forth in Example 16, except 2-(methylamino)acetic acid is used as the amine in step 6. The final step is as follows: a solution of (R/S)-2-tert-butoxycarbonylamino-2-[2-(2-ethoxycarbonylmethyl-methyl-amino)-ethyl]-6-(4,4,5,5-tetramethyl-[1,3,2]-dioxa-borolan-2-yl)-hexanoic acid ethyl ester (138 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 (72 mg, 76%); 1H NMR (D2O, 300 MHz) δ 3.94 (s, 2H), 3.37 (m, 1H), 3.20 (m, 1H), 2.83 (s, 3H), 2.24 (t, J=8 Hz, 2H), 1.66-1.88 (m, 2H), 1.27 (m, 3H), 1.11 (m, 1H) and 0.63 (t, J=7.5 Hz, 2H).

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-69772cf3884941978433fceb12632cc8
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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