1,1'-Carbonyldiimidazole → HCID 70000385, compound

HRID 1634799Notes

Reaction equation

HRID 1634799 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8]C(O)=O.[C:12]([O:16][C:17](=[O:36])[NH:18][CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH2:22][CH2:21]1)([CH3:15])([CH3:14])[CH3:13].[C:37](N1C=CN=C1)([N:39]1C=CN=C1)=[O:38]>C(Cl)Cl>[C:12]([O:16][C:17](=[O:36])[NH:18][CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:37]([NH:39][CH2:8][CH2:7][CH2:6][C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[O:38])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH2:22][CH2:21]1)([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 783864-(2-Thienyl)Butyric AcidHCID 23553541HCID 23553541, compound

Product 1

HCID 70000385HCID 70000385, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2-thienyl)butanoic acid (1.35 g, 7.90 mmol), [1-(4-aminobenzen-esulfonyl)-piperidin-4-ylmethyl]-carbamic acid t-butyl ester (2.90 g, 7.90 mmol) and carbonyldiimidazole (1.27 g, 7.9 mmol) in methylene chloride was stirred overnight at ambient temperature. The reaction mixture was washed with 1N NaOH, 1N HCl, and brine. The organic phase was dried (Na2SO4) and concentrated in vacuo to give near quantitative yield of the title compound.

Workup

  1. washThe reaction mixture was washed with 1N NaOH, 1N HCl, and brine
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43ce17b0cb654736a80152af4e763d48
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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