Triethylamine → HCID 131723212, compound

HRID 8846Notes

Reaction equation

HRID 8846 reaction equation
Cl[S:2]([CH2:5][C@H:6]([CH3:17])[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])(=[O:4])=[O:3].[CH2:18]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCN(CC)CC.C(OCC)(=O)C.CCCCCC>C(Cl)Cl>[CH2:18]([N:25]1[CH2:30][CH2:29][N:28]([S:2]([CH2:5][C@H:6]([CH3:17])[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])(=[O:4])=[O:3])[CH2:27][CH2:26]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 759941-BenzylpiperazineHCID 18738445HCID 18738445, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 131723212HCID 131723212, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 100 mL round bottom flask equipped with magnetic stirring bar and N2 inlet was charged with 2.5 g benzyl 3-chlorosulfonyl-2(R)-methylpropionate in 25 mL CH2Cl2. The solution was cooled to 0° C. and charged with 1.57 mL (1.0 eq.) 4-benzylpiperazine and 1.26 mL NEt3. The reaction was stirred for 1 hour then concentrated in vacuo and partitioned between ethyl acetate and saturated sodium bicarbonate. The combined organics were washed with brine, dried over Na2SO4, and concentrated in vacuo to yield 3.4 g crude product. Flash chromatography (80:20 ethyl acetate/hexane) yielded 3.0 g pure product.

Workup

  1. customA 100 mL round bottom flask equipped with magnetic stirring bar and N2 inlet
  2. concentrationthen concentrated in vacuo
  3. custompartitioned between ethyl acetate and saturated sodium bicarbonate
  4. washThe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto yield 3.4 g crude product

Sources & evidence

ORD record
ord-02bfd6ae3cc9411485ab357305a1bce2
Source dataset
uspto-grants-2006_08
Patent number
US07091219B2

Reaction notes

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