Hydrochloric Acid → HCID 66833169, compound

HRID 579509Notes

Reaction equation

HRID 579509 reaction equation
C(OC([NH:11][C:12]([CH2:31][N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)([CH2:18][CH2:19][CH2:20][CH2:21][B:22]1[O:26]C(C)(C)C(C)(C)[O:23]1)[C:13]([O:15]CC)=[O:14])=O)C1C=CC=CC=1.[ClH:38]>>[ClH:38].[ClH:38].[NH2:11][C:12]([CH2:31][N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)([CH2:18][CH2:19][CH2:20][CH2:21][B:22]([OH:26])[OH:23])[C:13]([OH:15])=[O:14]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 66833259HCID 66833259, compound

Product 1

HCID 66833169HCID 66833169, compound

Procedure

A solution of ethyl 2-(benzyloxycarbonylamino)-2-(piperidin-1-ylmethyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate (0.26 g, 0.51 mmol) in 6 N HCl (20 mL) was heated to a gentle reflux for 48 h. After cooling to room temperature, the solution was washed with dichloromethane (5×15 mL) and concentrated (aqueous layer). The resulting residue was dissolved in water (3 mL) and passed through cation exchange resin Dowex 50-200 eluted with 2 N ammonia (4 g resin was loaded on a column, washed successively with water, 1 N HCl, water to neutral pH, 2 N ammonia solution and water to neutral pH). Fractions containing product were concentrated, diluted with minimal water, acidified with 6 N HCl, frozen and lyophilized to give 2-amino-6-borono-2-(piperidin-1-ylmethyl)hexanoic acid dihydrochloride. (60 mg, 43%). 1H NMR (D2O) δ 3.64-3.53 (m, 1H), 3.34 (d, J=13.9 Hz, 1H), 3.05-3.03 (m, 2H), 2.93-2.91 (m, 3H), 1.76-1.67 (m, 5H), 1.53-1.46 (m, 3H), 1.31-1.30 (m, 3H), 1.09-1.07 (m, 1H), 0.70 (t, J=7.3 Hz, 2H). MS found for C12H25BN2O4 m/z[254(M−18+1)].

Workup

  1. temperaturea gentle reflux for 48 h
  2. washthe solution was washed with dichloromethane (5×15 mL)
  3. concentrationconcentrated (aqueous layer)
  4. dissolutionThe resulting residue was dissolved in water (3 mL)
  5. washeluted with 2 N ammonia (4 g resin
  6. washwashed successively with water, 1 N HCl, water to neutral pH, 2 N ammonia solution and water to neutral pH)
  7. additionFractions containing product
  8. concentrationwere concentrated
  9. additiondiluted with minimal water
  10. temperaturefrozen

Sources & evidence

ORD record
ord-86d74ac91e8e41b3a9ce148f810d39d7
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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