Hydrochloric Acid → HCID 9914774, compound

HRID 1977323Notes

Reaction equation

HRID 1977323 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:43])[C@@H:6]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[O:29][C:28]=3[CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CO.Cl>O.O1CCCC1>[CH2:36]([C:28]1[O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:27]=1[C:24]1[CH:23]=[CH:22][C:21]([C:18]2[CH:19]=[CH:20][C:15]([O:14][C@@H:6]([CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:5]([OH:43])=[O:4])=[CH:16][CH:17]=2)=[CH:26][CH:25]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 10721150HCID 10721150, compound

Product 1

HCID 9914774HCID 9914774, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (2.5 N, 10 mL) was added into a mixture of (2S)-2-[4′-(2-benzyl-benzofuran-3-yl)-biphenyl-4-yloxy]-3-phenyl-propionic acid methyl ester (2.5 g, 4.65 mmol), methyl alcohol (40 mL) and tetrahydrofuran (40 mL). The reaction mixture was stirred for 1 hour, poured into water, acidified with HCl (2 N), and extracted with ethyl ether. The organic extracts were dried over MgSO4. Evaporation and crystallization from ethyl ether/hexanes gave a white solid (2.32 g, 95% yield): mp 167-169; MS m/e 376 (M+);

Workup

  1. extractionextracted with ethyl ether
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and crystallization from ethyl ether/hexanes

Sources & evidence

ORD record
ord-991f7395d5b7425f81cb79b798e710f6
Source dataset
uspto-grants-2001_05
Patent number
US06232322B1

Reaction notes

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