Triethylamine → HCID 86736338, compound

HRID 1390807Notes

Reaction equation

HRID 1390807 reaction equation
[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:4])[CH:2]=[O:3].[O:13]1[CH2:17][CH2:16][O:15][CH:14]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C@H:24]1[C@@H:27]([NH:28][C:29](=[O:38])[CH2:30][O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26](=[O:39])[NH:25]1.C(N(CC)CC)C>O1CCCC1>[OH:3][CH:2]([N:25]1[C:26](=[O:39])[C@H:27]([NH:28][C:29](=[O:38])[CH2:30][O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@H:24]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH:14]1[O:13][CH2:17][CH2:16][O:15]1)[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11008258Benzyl glyoxylateHCID 70605998HCID 70605998, compound

Product 1

HCID 86736338HCID 86736338, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Freshly distilled benzyl glyoxylate (312 mg, 1.9 mmol) and freshly distilled tetrahydrofuran (15 ml) were stirred with 4A molecular sieves for one hour and then cooled in ice. To this solution was added the solid product from Example 5 (437 mg, 1.19 mmol) followed by the dropwise addition of triethylamine (240 mg, 2.37 mmol). The ice bath was removed and the reaction was stirred for 1.5 hours. The solution was filtered and the filtrate was evaporated to dryness. The residue was dissolved in chloroform and chromatographed on a silica gel column with a chloroform-ethyl acetate gradient as eluant to give the title product, 525 mg (83%).

Workup

  1. temperaturecooled in ice
  2. customThe ice bath was removed
  3. filtrationThe solution was filtered
  4. customthe filtrate was evaporated to dryness
  5. dissolutionThe residue was dissolved in chloroform
  6. customchromatographed on a silica gel column with a chloroform-ethyl acetate gradient as eluant

Sources & evidence

ORD record
ord-78c6334717464b6cba0f2c7d92fcca55
Source dataset
uspto-grants-1979_02
Patent number
US04140688

Reaction notes

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