Triethylamine → HCID 11223319, compound

HRID 1783650Notes

Reaction equation

HRID 1783650 reaction equation
C(Cl)(=O)C(Cl)=O.[NH:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([OH:18])=O)=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.Cl.[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]2[CH2:26][C@H:27]3[NH:38][CH2:37][CH2:36][C@@:33]4([C:34]=2[CH:35]=1)[C@H:28]3[CH2:29][CH2:30][CH2:31][CH2:32]4.C(N(CC)CC)C>C1COCC1>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]2[CH2:26][C@H:27]3[N:38]([C:16]([C:12]4[CH:11]=[C:10]5[C:15](=[CH:14][CH:13]=4)[NH:7][CH:8]=[CH:9]5)=[O:18])[CH2:37][CH2:36][C@@:33]4([C:34]=2[CH:35]=1)[C@H:28]3[CH2:29][CH2:30][CH2:31][CH2:32]4

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 742801H-Indole-5-Carboxylic AcidHCID 1156556936397-14-5

Product 1

HCID 11223319HCID 11223319, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Oxalyl chloride (15 ul, 0.14 mmol) at RT was added to a solution of indole-5-carboxylic acid (0.02 g, 0.12 mmol) in THF (1 ml). After stirring at RT for 10 h, the mixture was added THF (1 ml) followed by (+)-3-methoxy-morphinan hydrochloride (0.04 g, 0.12 mmol), then triethylamine (0.1 ml, 0.7 mmol) was added and stirred for 18 h. The reaction mixture was filtered and washed with ethyl acetate. The filtrate was washed with saturated Na2CO3 (5 ml), dried (Na2SO4), filtered and concentrated at reduced pressure to give a crude pale brown oil. The crude product was purified by column chromatographed eluting with (MeOH:CH2Cl2=1:10) to give a pale yellow oil (0.013 g, 28% yield).

Workup

  1. stirringstirred for 18 h
  2. filtrationThe reaction mixture was filtered
  3. washwashed with ethyl acetate
  4. washThe filtrate was washed with saturated Na2CO3 (5 ml)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. customto give a crude pale brown oil
  9. customThe crude product was purified by column
  10. customchromatographed
  11. washeluting with (MeOH:CH2Cl2=1:10)

Sources & evidence

ORD record
ord-6d7d1b76c64b4f4bb2e305aa3f7ffb72
Source dataset
uspto-grants-2009_03
Patent number
US07501433B2

Reaction notes

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