Hydrochloric Acid → {(S)-6-[(R)-4-piperazin-1-ylmethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

HRID 1422621Notes

Reaction equation

HRID 1422621 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:43])[CH2:5][C@H:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][C@H:16]3[C:24]4[C:19](=[C:20]([CH2:29][N:30]5[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]5)[C:21]([C:25]([F:28])([F:27])[F:26])=[CH:22][CH:23]=4)[CH2:18][CH2:17]3)=[CH:14][C:9]=2[O:8][CH2:7]1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.ClCCl>[CH3:2][O:3][C:4](=[O:43])[CH2:5][C@H:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][C@H:16]3[C:24]4[C:19](=[C:20]([CH2:29][N:30]5[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]5)[C:21]([C:25]([F:26])([F:27])[F:28])=[CH:22][CH:23]=4)[CH2:18][CH2:17]3)=[CH:14][C:9]=2[O:8][CH2:7]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 90314350{(S)-6-[(R)-4-(4-tert-Butoxycarbonyl-piperazin-1-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Product 1

HCID 90313619{(S)-6-[(R)-4-piperazin-1-ylmethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

4 M HCl in 1,4-dioxane (5 mL) is added to a solution of {(S)-6-[(R)-4-(4-tert-butoxycarbonyl-piperazin-1-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (0.42 g) in dichloromethane (5 mL) at room temperature. The solution is stirred at room temperature for 2.5 h. The solution is basified with aqueous K2CO3 solution and extracted with dichloromethane. The combined extract is dried (Na2SO4) and concentrated to give the crude title compound that is used without further purification in subsequent transformations. LC (method 4): tR=0.98 min; Mass spectrum (ESI+): m/z=491 [M+H]+.

Workup

  1. extractionextracted with dichloromethane
  2. extractionThe combined extract
  3. dry with materialis dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8c5e8511a40e47c8ac46e017a939629e
Source dataset
uspto-grants-2015_01
Patent number
US08927531B2

Reaction notes

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