Hydrochloric Acid → HCID 57695565, compound

HRID 2079864Notes

Reaction equation

HRID 2079864 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[C:15]([C:17]3[N:21]([CH2:22][CH2:23][CH2:24][O:25][CH3:26])[N:20]=[N:19][N:18]=3)[C:14]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:13][C:12]=2[O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].[Li+].[OH-].Cl>C1COCC1.O>[CH2:36]([O:35][C:12]1[CH:13]=[C:14]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:15]([C:17]2[N:21]([CH2:22][CH2:23][CH2:24][O:25][CH3:26])[N:20]=[N:19][N:18]=2)=[CH:16][C:11]=1[C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57695605HCID 57695605, compound

Product 1

HCID 57695565HCID 57695565, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

2′,4′-Bis-benzyloxy-5′-[1-(3-methoxy-propyl)-1H-tetrazol-5-yl]-biphenyl-3-carboxylic acid methyl ester (1 mmol) was dissolved in mixture of THF (5 ml) and water (5 ml). LiOH (72 mg, 3 mmol) was added, and the resulting mixture was stirred at 80° C. overnight. After the reaction was complete, the reaction was cooled to r.t., acidified with 1M HCl to pH=1. After extraction with ether (25 ml×3), the combined organics were washed with water (25 ml) and saturated brine (25 ml) and dried over Na2SO4. After filtration and concentration, 2′,4′-bis-benzyloxy-5′-[1-(3-methoxy-propyl)-1H-tetrazol-5-yl]-biphenyl-3-carboxylic acid was obtained as white solid in quantitative yield. M.p.: 59-63° C.; 400 MHz 1H NMR (DMSO-d6) δ: 12.98 (br s, 1H), 8.18 (t, J=1.6 Hz, 1H), 7.89 (d, J=7.6 Hz, 1H), 7.78 (d, J=7.6 Hz, 1H), 7.54-7.28 (m, 13H), 5.32 (s, 2H), 5.31 (s, 2H), 4.27 (t, J=7.2 Hz, 2H), 3.18 (t, J=6.0 Hz, 2H), 3.06 (s, 3H), 1.93 (pent, J=6.8 Hz, 2H); LCMS: 551 [M+H].

Workup

  1. temperaturethe reaction was cooled to r.t.
  2. extractionAfter extraction with ether (25 ml×3)
  3. washthe combined organics were washed with water (25 ml) and saturated brine (25 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-6afcdaee4ea844268231bae7833a3b1f
Source dataset
uspto-grants-2011_04
Patent number
US07932279B2

Reaction notes

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