Acetic Acid → 1-(1-(4-(5-Benzylbenzofuran-2-yl)-3-fluorophenyl)ethyl)azetidine-3-carboxylic acid

HRID 2075275Notes

Reaction equation

HRID 2075275 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]([OH:7])=[O:6])[CH2:2]1.[CH2:8]([C:15]1[CH:16]=[CH:17][C:18]2[O:22][C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29](=O)[CH3:30])=[CH:25][C:24]=3[F:32])=[CH:20][C:19]=2[CH:33]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH2:8]([C:15]1[CH:16]=[CH:17][C:18]2[O:22][C:21]([C:23]3[CH:28]=[CH:27][C:26]([CH:29]([N:1]4[CH2:4][CH:3]([C:5]([OH:7])=[O:6])[CH2:2]4)[CH3:30])=[CH:25][C:24]=3[F:32])=[CH:20][C:19]=2[CH:33]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 931923-azetidinecarboxylic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 584153111-(4-(5-Benzylbenzofuran-2-yl)-3-fluorophenyl)ethanone

Product 1

HCID 248504121-(1-(4-(5-Benzylbenzofuran-2-yl)-3-fluorophenyl)ethyl)azetidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of azetidine-3-carboxylic acid (0.015 g, 0.15 mmol), 1-(4-(5-benzylbenzofuran-2-yl)-3-fluorophenyl)ethanone (0.050 g, 0.15 mmol), acetic acid (0.013 mL, 0.22 mmol) in methanol (3.0 mL) was stirred at room temperature for 1 h. Sodium triacetoxyborohydride (0.037 g, 0.17 mmol) was added and the mixture was stirred for 1 h at room temperature. Evaporation and purification by flash chromatography (5% AcOH in CHCl3 and MeOH). The resulting solid was suspended in in an aqueous buffered solution (pH 6, phosphate buffer) and sonicated. The solids were collected by filtration, washed with water and Et2O to give title compound [hS1P1 EC50=313 nM]. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.89 (t, J=7.9 Hz, 1H), 7.51-7.59 (m, 2H), 7.14-7.34 (m, 9H), 4.04 (s, 2H), 2.92-3.50 (m, 6H partially overlapping with HDO signal), 1.11 (d, J=6.3 Hz, 3H). MS (ESI) m/z: Calculated; 429.2 Observed: 430.2 (M++1).

Workup

  1. stirringthe mixture was stirred for 1 h at room temperature
  2. customEvaporation and purification by flash chromatography (5% AcOH in CHCl3 and MeOH)
  3. customsonicated
  4. filtrationThe solids were collected by filtration
  5. washwashed with water and Et2O

Sources & evidence

ORD record
ord-0018e419c8754118a534506cb00951eb
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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