tert-butyl N-(4-aminobutyl)carbamate → 3-[(Phenylsulfonyl)amino]-N-(4-aminobutyl)benzamide

HRID 1599530Notes

Reaction equation

HRID 1599530 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([P+](ON1N=NC2C1=CC=CC=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[NH2:47][CH2:48][CH2:49][CH2:50][CH2:51][NH:52]C(OC(C)(C)C)=O.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([NH:47][CH2:48][CH2:49][CH2:50][CH2:51][NH2:52])=[O:16])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7922013-Benzenesulfonamidobenzoic acid

Product 1

HCID 189289463-[(Phenylsulfonyl)amino]-N-(4-aminobutyl)benzamideYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(Phenylsulfonyl)aminobenzoic acid as prepared in Example 9 (139 mg, 0.5 mmol), Castro's reagent (benzotriazole-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate) (221 mg, 0.5 mmol), tert-butyl 4-aminobutylaminocarboxylate (100 mg, 0.6 mmol) and triethylamine (0.2 mL) were mixed in dry DMF (5 mL) and stirred at room temperature for 3 hours. The mixture was dissolved in ethyl acetate (100 mL) and washed with saturated NaHCO3 (2×50 mL), brine (2×50 mL) and dried over Na2SO4. After evaporation of the solvent, the residue was mixed with 1:1 trifluoroacetic acid (TFA):CH2Cl2 (10 mL), stirred at room temperature for 2 hours and the solvent evaporated to give the title compound (140 mg, 81%) as the TFA salt. 1H-NMR (300 MHz, DMSO-d6): δ 1.17 (m, 4H), 2.79 (t, 2H), 3.23 (d, 2H), 7.23 (d, 1H), 7.30 (t, 1H), 7.57 (m, 5H), 7.60 (d, 2H), 8.50 (t, 1H). Mass spectrum (MALDI-TOF) calcd. for C17H21 N3O3S: 370.4 (M+Na), Found: 370.7.

Workup

  1. washwashed with saturated NaHCO3 (2×50 mL), brine (2×50 mL)
  2. dry with materialdried over Na2SO4
  3. customAfter evaporation of the solvent
  4. additionthe residue was mixed with 1:1 trifluoroacetic acid (TFA)
  5. stirringCH2Cl2 (10 mL), stirred at room temperature for 2 hours
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-12df5cfd6dad4d21bcfda599fab9773f
Source dataset
uspto-grants-1998_04
Patent number
US05741819

Reaction notes

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