Propionic Acid → HCID 20196392, compound

HRID 652801Notes

Reaction equation

HRID 652801 reaction equation
B.[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH2:17][CH2:18][NH:19][C:20](=O)[CH:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:25][CH:24]=2)[OH:22])[CH:13]=[CH:14][C:15]=1[OH:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O)(=O)CC>O1CCCC1>[CH2:30]([O:29][C:26]1[CH:25]=[CH:24][C:23]([CH:21]([OH:22])[CH2:20][NH:19][CH2:18][CH2:17][C:12]2[CH:13]=[CH:14][C:15]([OH:16])=[C:10]([O:9][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH:11]=2)=[CH:28][CH:27]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 1032Propionic AcidHCID 6331BoraneHCID 20196416HCID 20196416, compound

Product 1

HCID 20196392HCID 20196392, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

148 ml of 1.67M boron hydride in tetrahydrofurane were added to a solution of 11.3 g of N-[2-(3-benzyloxy-4-hydroxyphenyl)-ethyl]-4-benzyloxy-mandelamide (obtained as described in example 67) in 100 ml of tetrahydrofurane. After 3 hours under reflux, the mixture was cooled and 6.93 g of propionic acid were added. The mixture was refluxed again for 1 hour and then evaporated to dryness. The resulting oil was dissolved in methylene chloride, washed with water and diluted sodium hydroxide, dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by chromatography on silica gel column using methylene chloride/methanol/ammonium hydroxide=97/3/0.3 as eluent. N-[2-(4-Benzyloxyphenyl)-2-hydroxyethyl]-3-O-benzyldopamine was thus obtained, m.p. 124°-125° C. (from ethanol).

Workup

  1. temperatureAfter 3 hours under reflux
  2. temperaturethe mixture was cooled
  3. temperatureThe mixture was refluxed again for 1 hour
  4. customevaporated to dryness
  5. dissolutionThe resulting oil was dissolved in methylene chloride
  6. washwashed with water and diluted sodium hydroxide
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe residue was purified by chromatography on silica gel column

Sources & evidence

ORD record
ord-9e268d8adfdf457f9ce1e17293d0f1ee
Source dataset
uspto-grants-1987_06
Patent number
US04673671

Reaction notes

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