Triethylamine → HCID 86690057, compound

HRID 539407Notes

Reaction equation

HRID 539407 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([C:17]2([C:23]([O:25][CH3:26])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:32][CH3:33])CC)C>>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([S:14]([C:17]2([C:23]([O:25][CH3:26])=[O:24])[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:33]3[CH:32]=[CH:4][CH:3]=[CH:2][CH:7]=3)=[O:24])[CH2:19][CH2:18]2)(=[O:16])=[O:15])=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8471TriethylamineHCID 86690058HCID 86690058, compound

Product 1

HCID 86690057HCID 86690057, compound

Procedure

1-Benzyl 4-methyl 4-((4-phenoxyphenyl)sulfonyl)piperidine-1,4-dicarboxylate was synthesized as shown in FIG. 10. A 100 ml RBF equipped with magnetic stir bar was charged with 1.1 g (2.67 mmole) 4-methyl 4-((4-phenoxyphenyl)sulfonyl)piperidine-4-carboxylate 0.73 g (2.94 mmole) Cbz-OSu, 0.8 g (8.01 mmole) triethylamine. LCMS after 1 hour showed complete reaction with M+H=510 g/mol. The reaction was partitioned between EA and satd. aq. sodium bicarbonate. The organics were washed with 10 aq. KHSO4, dried and concentrated to thick syrup that turned into white dry foam upon high vacuum drying. The product was dried overnight to afford 1.29 g (95% yield) of the Cbz ester that was used in Step 2.

Workup

  1. customA 100 ml RBF equipped with magnetic stir bar
  2. customreaction with M+H=510 g/mol
  3. customThe reaction was partitioned between EA
  4. washThe organics were washed with 10 aq. KHSO4
  5. customdried
  6. concentrationconcentrated to thick syrup that
  7. custominto white dry foam upon high vacuum
  8. customdrying
  9. customThe product was dried overnight

Sources & evidence

ORD record
ord-412106227efe4e369feaead18dd00938
Source dataset
uspto-grants-2014_10
Patent number
US08871189B2

Reaction notes

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