Diisopropylethylamine → HCID 69037612, compound

HRID 1820713Notes

Reaction equation

HRID 1820713 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 trifluoroacetic 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-6af6e5e6d9154c58b90ca1f1824e0ab3
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

Loading…