Hydrochloric Acid → HCID 66833342, compound

HRID 579580Notes

Reaction equation

HRID 579580 reaction equation
C([NH:4][C:5]([C@@H:26]1[CH2:30][CH2:29][N:28]([S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[N+:40]([O-:42])=[O:41])(=[O:33])=[O:32])[CH2:27]1)([CH2:13][CH2:14][CH2:15][CH2:16][B:17]1[O:21]C(C)(C)C(C)(C)[O:18]1)[C:6](NC(C)(C)C)=[O:7])(=O)C.[O:43]1CCOCC1.Cl>O>[NH2:4][C:5]([C@@H:26]1[CH2:30][CH2:29][N:28]([S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[N+:40]([O-:42])=[O:41])(=[O:32])=[O:33])[CH2:27]1)([CH2:13][CH2:14][CH2:15][CH2:16][B:17]([OH:18])[OH:21])[C:6]([OH:43])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66833675HCID 66833675, compound

Product 1

HCID 66833342HCID 66833342, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-acetamido-N-tert-butyl-2-((R)-1-(2-nitrophenylsulfonyl)pyrrolidin-3-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide (500 mg, 0.8 mmol) in 1,4-dioxane (3 mL, 40 mmol) was treated with a 6M aqueous solution of hydrogen chloride (6 mL, 40 mmol) followed by heating to 100° C. for 24 h. At the end of the 24 hour period, the reaction mixture was diluted with water and filtered. The filtrate that was obtained was purified by HPLC using 5%-50% acetonitrile in water over 30 min. The product-containing fractions were concentrated, then dissolved in 1N HCl and frozen prior to lyophilization to afford 2-amino-6-borono-2-((R)-1-(2-nitrophenylsulfonyl)pyrrolidin-3-yl)hexanoic acid (79 mg, 20%) as a white foam. 1H NMR (400 MHz, DMSO-d6, Mixture of diastereoisomers) δ 8.55-8.35 (2H), 8.05-7.98 (m, 2H), 7.96-7.85 (m, 2H), 5.83 (t, J=6.5 Hz, 2H), 3.70-3.14 (m, 4H), 2.78-2.65 (m, 1H), 2.19-1.60 (m, 4H), 1.47-1.23 (m, 3H), 1.14-1.00 (m, 1H); ESI MS found for C16H24BN3O8S m/z 412.1 [M−OH)+; 410.2 (M−H2O)−.

Workup

  1. filtrationfiltered
  2. customThe filtrate that was obtained
  3. customwas purified by HPLC
  4. customover 30 min
  5. concentrationThe product-containing fractions were concentrated
  6. dissolutiondissolved in 1N HCl
  7. temperaturefrozen

Sources & evidence

ORD record
ord-34c3c861594d4b599ebb5ae2d378b65b
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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