Hydrochloric Acid → HCID 77847525, compound

HRID 1422638Notes

Reaction equation

HRID 1422638 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[N:8]1([CH2:14][C:15]2[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[C:20]3[C:16]=2[CH2:17][CH2:18][C@H:19]3[O:28][C:29]2[CH:41]=[CH:40][C:32]3[C@H:33]([CH2:36][C:37]([OH:39])=[O:38])[CH2:34][O:35][C:31]=3[CH:30]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(N(CC)C(C)C)(C)C.[OH-].[Na+].Cl>C(#N)C.O>[C:1]([N:11]1[CH2:12][CH2:13][N:8]([CH2:14][C:15]2[C:23]([C:24]([F:26])([F:25])[F:27])=[CH:22][CH:21]=[C:20]3[C:16]=2[CH2:17][CH2:18][C@H:19]3[O:28][C:29]2[CH:41]=[CH:40][C:32]3[C@H:33]([CH2:36][C:37]([OH:39])=[O:38])[CH2:34][O:35][C:31]=3[CH:30]=2)[CH2:9][CH2:10]1)(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 77847439HCID 77847439, compound

Product 1

HCID 77847525HCID 77847525, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Acetic anhydride (0.03 mL) is added to a solution of {(S)-6-[(R)-4-piperazin-1-ylmethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid (0.22 g) and N,N-diisopropyl-ethylamine (0.11 mL) in acetonitrile (5 mL) at room temperature. The solution is stirred at room temperature for 1.5 h. 4 M aqueous NaOH solution (0.1 mL) is added and the solution is stirred for another 30 min. Water is added and the resulting solution is acidified with 4 M HCl solution (pH ca. 3-4). The resulting mixture is extracted with ethyl acetate, and the combined extracts are washed with brine and dried (Na2SO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate) to give the title compound. LC (method 1): tR=0.95 min; Mass spectrum (ESI+): m/z=519 [M+H]+.

Workup

  1. stirringthe solution is stirred for another 30 min
  2. extractionThe resulting mixture is extracted with ethyl acetate
  3. washthe combined extracts are washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent is evaporated
  6. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-332690f5688445828a70addd90644788
Source dataset
uspto-grants-2015_01
Patent number
US08927531B2

Reaction notes

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