Methanol → HCID 15617483, compound

HRID 1031636Notes

Reaction equation

HRID 1031636 reaction equation
C(N(CC)CC)C.[SH:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12].C(CCS[CH:22]([CH:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)O)[C:23]([O:25][CH3:26])=[O:24])(OC)=O.C[OH:50]>>[C:11]([CH2:10][CH2:9][S:8][CH:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[CH:22]([OH:50])[C:23]([O:25][CH3:26])=[O:24])([O:13][CH3:14])=[O:12]

Participants

5

Reactant 4

HCID 887Methanol2×HCID 8471Triethylamine2×HCID 18050Methyl 3-mercaptopropionateHCID 19023803HCID 19023803, compound

Product 1

HCID 15617483HCID 15617483, compound

Procedure

The compound of Example 3(a) (1.2 g, 3.28 mmoles) was dissolved in methanol (20 ml) containing 2% triethylamine and stirred under argon at room temperature. Methyl 3-mercaptopropionate (0.623 ml, 5.45 mmoles) and triethylamine (1.45 ml, 9.84 mmoles) were dissolved in methanol (15 ml) and added dropwise. The mixture was stirred for 18 hours. The solvent was stripped and the residue was flash chromatographed on silica gel eluted with 20% ethyl acetate/hexane to give a mixture of the desired product and its regioisomer, methyl 2-(2-carbomethoxyethylthio)-3-[2-(8 phenyloctyl)phenyl]-3-hydroxypropanoate. The mixture was rechromatographed on 100 grams of neutral alumina to separate the desired product.

Workup

  1. additionadded dropwise
  2. stirringThe mixture was stirred for 18 hours
  3. customchromatographed on silica gel
  4. washeluted with 20% ethyl acetate/hexane
  5. customto give

Sources & evidence

ORD record
ord-2cadb970dcf24e4e9a92ccd062a50da7
Source dataset
uspto-grants-1990_09
Patent number
US04954513

Reaction notes

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