Diisopropylethylamine → HCID 69037612, compound

HRID 2251168Notes

Reaction equation

HRID 2251168 reaction equation
[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][C:6]=1[C:7]([OH:9])=O)([CH3:3])[CH3:2].[N:18]1([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C>>[C:27]([O:26][C:24]([N:18]1[CH2:23][CH2:22][N:21]([C:7](=[O:9])[C:6]2[CH:10]=[C:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:12]=[CH:13][C:5]=2[O:4][CH:1]([CH3:2])[CH3:3])[CH2:20][CH2:19]1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 211002372-Isopropoxy-5-methylsulfonylbenzoic acid2×

Product 1

HCID 69037612HCID 69037612, compoundYield 96.9%

Procedure

A solution of 2-isopropoxy-5-methanesulfonyl-benzoic acid (compound 1.2, 1.0 g), tert-butyl 1-piperazinecarboxylate (0.78 g), TBTU (1.4 g) and N-ethyldiisopropylamine (4 mL) was stirred at room temperature for 2 hours. After such time, the reaction mixture was concentrated in vacuo and purified by column chromatography (SiO2) to give 4-(2-Isopropoxy-5-methanesulfonyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester as a colorless foam (1.6 g). The latter was dissolved in dichloromethane (11 mL) and treated with trifluroacetic acid (4.2 mL) for 30 minutes. After such time the reaction mixture was concentrated in vacuo to yield the title compound (1.6 g) as light yellow oil. MS (m/e): 327.1 (M+H+, 100%).

Workup

  1. concentrationAfter such time, the reaction mixture was concentrated in vacuo
  2. custompurified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-d9b6e30c237e49859c03c978180b07d9
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

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