Diethylamine → (4-Diethylaminomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid

HRID 1798088Notes

Reaction equation

HRID 1798088 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:18])[CH:14]=[C:15]([CH2:16]Br)[C:7]1=2)C.[CH2:20]([NH:22][CH2:23][CH3:24])[CH3:21]>C(Cl)Cl>[CH2:20]([N:22]([CH2:16][C:15]1[C:7]2[CH:6]([CH2:5][C:4]([OH:3])=[O:19])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=[C:13]([OH:18])[CH:14]=1)[CH2:23][CH3:24])[CH3:21]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 58292861(4-Bromomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester

Product 1

HCID 58292864(4-Diethylaminomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (4-Bromomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.5 mmol) in DCM (5 mL) was added diethylamine (5 mmol) and the mixture was stirred overnight at r.t. The crude product was evaporated, LiOH (75 mg) in THF/water/methanol (2:1:1, 5 mL) was added and stirred at r.t. for 1 h. The solvent was evaporated to give a residue, which was purified by HPLC, yielded 5 mg of desire product. MS (ESI) m/z: 294 [M+1]+; 1H NMR (300 MHz, CD3OD) δ 7.18 (s, 2H), 5.72-5.76 (dd, 1H), 4.20-4.45 (dd, 2H), 3.05-3.22 (m, 3H), 2.36-2.44 (dd, 1H), 1.40-1.45 (t, 3H), 1.30-1.34 (t, 3H).

Workup

  1. customThe crude product was evaporated
  2. additionLiOH (75 mg) in THF/water/methanol (2:1:1, 5 mL) was added
  3. stirringstirred at r.t. for 1 h
  4. customThe solvent was evaporated
  5. customto give a residue, which
  6. customwas purified by HPLC
  7. customyielded 5 mg of desire product

Sources & evidence

ORD record
ord-ddd7a49fc6054c9bafe27eea7567f563
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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