Methanol → HCID 19023769, compound

HRID 1034316Notes

Reaction equation

HRID 1034316 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[CH:14]=[CH:13][C:12]([SH:15])=[CH:11][CH:10]=1.O[CH:17]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH:18](SC1C=CC(O)=CC=1)[C:19]([O:21][CH3:22])=[O:20].C[OH:52]>>[OH:52][CH:18]([CH:17]([S:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 4

HCID 887Methanol2×HCID 8471Triethylamine2×HCID 2401474-MercaptophenolHCID 19023818HCID 19023818, compound

Product 1

HCID 19023769HCID 19023769, compound

Procedure

The compound of Example 1(c) (722 mg, 2 mmol) was dissolved in methanol (10 ml) containing 2% triethylamine and the solution was stirred under argon at room temperature. Triethylamine (1.68 ml, 12 mmol) and 4-hydroxythiophenol (428 mg, 3.4 mmol) were dissolved in methanol (15 ml) and added to the reaction mixture which was then stirred overnight at room temperature. The solvent was evaporated and the residue was flash chromatographed on 80 grams of silica gel eluted with 30% ethyl acetate/hexane to give a mixture of the desired product and its regioisomer, methyl 3-hydroxy-2-(4-hydroxyphenylthio)-3[2-(8-phenyloctyl)phenyl]propionate. The mixture of regioisomers was dissolved in methanol (20 ml) and stirred under argon at room temperature. Sodium methoxide, 25 wt. % in methanol, (0-92 ml, 4 mmol) was added dropwise and the mixture-stirred for 2.5 hours. The mixture was cooled in an ice bath and acetic acid (0.3 ml, 5.2 mmol) was added dropwise. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated to give the crude product which was flash chromatographed on 80 grams of silica gel eluted with 25% ethyl acetate/hexane to give the desired product.

Workup

  1. additionadded to the reaction mixture which
  2. stirringwas then stirred overnight at room temperature
  3. customThe solvent was evaporated
  4. customchromatographed on 80 grams of silica gel
  5. washeluted with 30% ethyl acetate/hexane
  6. customto give

Sources & evidence

ORD record
ord-25257ff65af3421192c63934c8fe0db5
Source dataset
uspto-grants-1994_05
Patent number
US05314918

Reaction notes

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