Water → (2R,3S)-3-amino-2-(3-boronopropyl)tetrahydrofuran-3-carboxylic acid

HRID 61351Notes

Reaction equation

HRID 61351 reaction equation
C([NH:4][C@@:5]1([C:22](NC(C)(C)C)=[O:23])[CH2:9][CH2:8][O:7][C@@H:6]1[CH2:10][CH2:11][CH2:12][B:13]1[O:17]C(C)(C)C(C)(C)[O:14]1)(=O)C.[OH2:29]>Cl>[NH2:4][C@@:5]1([C:22]([OH:23])=[O:29])[CH2:9][CH2:8][O:7][C@@H:6]1[CH2:10][CH2:11][CH2:12][B:13]([OH:14])[OH:17]

Participants

4

Reactant 2

HCID 962WaterHCID 67516397(2R,3S)-3-acetamido-N-tert-butyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)tetrahydrofuran-3-carboxamide

Product 1

HCID 57331353(2R,3S)-3-amino-2-(3-boronopropyl)tetrahydrofuran-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (2R,3S)-3-acetamido-N-tert-butyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)tetrahydrofuran-3-carboxamide (860 mg) in 6 N HCl (15 mL) was stirred at 90° C. for 1 day. After cooling to room temperature, the reaction mixture was transferred to a separator funnel, diluted with deionized water (10 mL) and washed with dichloromethane (3×). The aqueous solution was concentrated. Purification by RP-HPLC (10-100% acetonitrile in water) gave (2R,3S)-3-amino-2-(3-boronopropyl)tetrahydrofuran-3-carboxylic acid, as a white solid (269 mg). 1H NMR (D2O, 300 MHz) δ 3.97 (m, 2 H), 3.82 (m, 1 H), 2.66 (ddd, J1=15 Hz, J2=9.5 Hz, J3=5.5 Hz, 1 H), 2.14 (ddd, J1=15 Hz, J2=9 Hz, J3=6.5 Hz, 1 H), 1.22-1.49 (m, 4 H), 0.67 (m, 2 H); MS (+CI): m/z for C8H16BlNO5: expected 217.1; found 435.3 (2M+H)+, 417.2 (2M+H−H2O)+, 217.7 (M+H)+, 200.0 (M+H−2H2O)+.

Workup

  1. customthe reaction mixture was transferred to a separator funnel
  2. washwashed with dichloromethane (3×)
  3. concentrationThe aqueous solution was concentrated
  4. customPurification by RP-HPLC (10-100% acetonitrile in water)

Sources & evidence

ORD record
ord-93997f056f8345a0a06cf4b497ab5885
Source dataset
uspto-grants-2016_09
Patent number
US09440995B2

Reaction notes

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