Hydrochloric Acid → HCID 66833416, compound

HRID 579571Notes

Reaction equation

HRID 579571 reaction equation
C([NH:4][C:5]([C@@H:26]1[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]1)([C:19](=[O:25])NC(C)(C)C)[CH2:6][CH2:7][CH2:8][CH2:9][B:10]1[O:14]C(C)(C)C(C)(C)[O:11]1)(=O)C.[ClH:38].[OH2:39]>O1CCOCC1>[ClH:38].[ClH:38].[NH2:4][C@@:5]([C@@H:26]1[CH2:30][CH2:29][NH:28][CH2:27]1)([CH2:6][CH2:7][CH2:8][CH2:9][B:10]([OH:11])[OH:14])[C:19]([OH:25])=[O:39]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 66832736HCID 66832736, compound

Product 1

HCID 66833416HCID 66833416, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a 50 ML round bottom flask, tert-butyl (3R)-3-[1-acetamido-1-(tert-butylcarbamoyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentyl]pyrrolidine-1-carboxylate (1.41 g, 2.69 mmol) was dissolved in 1,4-dioxane (10 mL). To this solution was added a 6M aqueous solution of hydrogen chloride (10 mL) in a single portion and the reaction was heated under refluxing conditions for 18 h. At the end of 18 hours the reaction mixture was cooled to room temperature prior to dilution with water (10 mL). The aqueous layer was washed with ethyl acetate (20 mL) and concentrated in vacuo prior to lyophilization to afford (R)-2-amino-6-borono-2-((R)-pyrrolidin-3-yl)hexanoic acid dihydrochloride (0.657 g) as a mixture of diastereomers. The crude foam was used without purification in the next step. ESI MS found for C10H21BN2O4 m/z 227.2 (M+H-water)+.

Workup

  1. temperaturethe reaction was heated under refluxing conditions for 18 h
  2. washThe aqueous layer was washed with ethyl acetate (20 mL)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7efaaa7438cc4dd68edbacc8d8064492
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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