Adipic Acid → HCID 18374588, compound

HRID 2300705Notes

Reaction equation

HRID 2300705 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH:14]([OH:15])[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:16][CH3:17])[CH2:12][S:11](=[O:23])(=[O:22])[C:10]3[CH:24]=[CH:25][C:26]([N:28]([CH3:30])[CH3:29])=[CH:27][C:9]2=3)[CH:5]=[CH:6][CH:7]=1.[C:31](O)(=[O:39])[CH2:32][CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37].C1(N=C=NC2CCCCC2)CCCCC1.N1(O)C2C=CC=CC=2N=N1>O1CCCC1>[CH2:18]([C:13]1([CH2:16][CH3:17])[CH2:12][S:11](=[O:22])(=[O:23])[C:10]2[CH:24]=[CH:25][C:26]([N:28]([CH3:29])[CH3:30])=[CH:27][C:9]=2[CH:8]([C:4]2[CH:3]=[C:2]([NH:1][C:31]([CH2:32][CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[O:39])[CH:7]=[CH:6][CH:5]=2)[CH:14]1[OH:15])[CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 196Adipic AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 18374573HCID 18374573, compound

Product 1

HCID 18374588HCID 18374588, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 g of 5-(3-aminophenyl)-3-butyl-7-dimethylamino-3-ethyl-1,1-dioxo-2,3,4,5-tetra-hydro-1H-benzo[b]thiepin-4-ol, 3.4 g of hexanedioic acid, 1.04 g of dicyclohexylcarbodiimide and 640 mg of benzotriazol-1-ol in 80 ml of tetrahydrofuran are stirred at room temperature overnight. The mixture is concentrated, the residue is taken up in ethyl acetate, excess urea is removed by filtration and the mixture is washed with water. The residue of the dried organic phase is purified by column filtration (SiO2, dichloromethane/methanol=20:1). This gives the product of molecular weight 558.7 (C30H42N2O6S); MS (ESI+): 559 (M+H+).

Workup

  1. concentrationThe mixture is concentrated
  2. customexcess urea is removed by filtration
  3. washthe mixture is washed with water
  4. filtrationThe residue of the dried organic phase is purified by column filtration (SiO2, dichloromethane/methanol=20:1)
  5. customThis gives the product of molecular weight 558.7 (C30H42N2O6S)

Sources & evidence

ORD record
ord-4eeba6f0ecd74c7d8d6eac35538b03e0
Source dataset
uspto-grants-2002_12
Patent number
US06498156B2

Reaction notes

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