Hydrochloric Acid → HCID 10554409, compound

HRID 1977334Notes

Reaction equation

HRID 1977334 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C([O:13][C:14](=[O:53])[C:15]([O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([C:37]3[C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=4[O:39][C:38]=3[CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[CH:33][CH:32]=2)=[CH:27][CH:26]=1)([CH3:23])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)C.C(Br)C1C=CC=CC=1.Cl>O.O1CCCC1>[CH2:46]([C:38]1[O:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[C:37]=1[C:34]1[CH:33]=[CH:32][C:31]([C:28]2[CH:29]=[CH:30][C:25]([O:24][C:15]([CH3:23])([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:14]([OH:53])=[O:13])=[CH:26][CH:27]=2)=[CH:36][CH:35]=1)[C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 2733832Lithium HexamethyldisilazideHCID 54201845HCID 54201845, compound

Product 1

HCID 10554409HCID 10554409, compoundYield 47.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-45 °C

Procedure

Lithium bis(trimethylsilyl)amide (1.0 M, 1.68 mL, 1.68 mmol) was added dropwise into a cold (−78° C.) mixture of 2-[4′-(2-benzyl-benzofuran-3-yl)-biphenyl-4-yloxy]-2-methyl-3-phenyl-propionic acid ethyl ester (0.8 g, 1.68 mmol), and tetrahydrofuran (8.0 mL). The mixture was allowed to gradually warm up to −45° C., and stirred for 2 hours. Benzyl bromide (0.29 mL, 2.52 mmol) was added into the reaction mixture. The temperature was gradually raised to room temperature and the reaction was stirred for 15 hours. The mixture was then poured in to water, acidified with HCl (2 N) to pH=5, and extracted with ethyl acetate. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography on silica gel (hexanes/EtAOc 5:1) gave an clear oil (0.43 g). The product was saponified according to Example 1 step h, to give a white solid (0.32 g, 34% yield for two steps): MS m/e 538 (M+);

Workup

  1. temperatureThe temperature was gradually raised to room temperature
  2. stirringthe reaction was stirred for 15 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic extracts were dried over MgSO4
  5. customEvaporation and purification by flash chromatography on silica gel (hexanes/EtAOc 5:1)

Sources & evidence

ORD record
ord-713645ff27b04cc3a9b10c2b9a6b06be
Source dataset
uspto-grants-2001_05
Patent number
US06232322B1

Reaction notes

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