N-(1,1-Dimethylethyl)benzenamine → 5-{4-[(4-Tert-butylphenylamino)methyl]phenyl}-penta-2,4-dienoic acid

HRID 480373Notes

Reaction equation

HRID 480373 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][CH:11]=[CH:12][C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1)=O.C([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(C)(C)C.C[C@H](NC([C@H]1N(C([C@@H](NC([C@@H](N)[CH2:93][C:94]2[CH:99]=CC(O)=C[CH:95]=2)=O)CC(O)=O)=O)CCC1)=O)C(N1[C@H](C(N2[C@H](C(N3[C@H](C(N4[C@H](C(N5[C@H](C(N6[C@H](C(O)=O)CCC6)=O)CCC5)=O)CCC4)=O)CCC3)=O)CCC2)=O)CCC1)=O.C([BH3-])#N.[Na+]>CN1C(=O)CCC1.CN(C=O)C.CN(C=O)C.CO.CC(O)=O>[C:94]([C:24]1[CH:23]=[CH:22][C:21]([NH:20][CH2:1][C:3]2[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][CH:11]=[CH:12][C:13]([OH:15])=[O:14])=[CH:5][CH:4]=2)=[CH:26][CH:25]=1)([CH3:99])([CH3:95])[CH3:93]

Participants

9

Reactant 4

HCID 254260N-(1,1-Dimethylethyl)benzenamineHCID 5003444Sodium cyanoborohydrideHCID 5488810Peptide oostatic hormoneHCID 734625515-(4-Formylphenyl)penta-2,4-dienoic acid

Product 1

HCID 734625565-{4-[(4-Tert-butylphenylamino)methyl]phenyl}-penta-2,4-dienoic acid

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

Resin linked 5-(4-formylphenyl)penta-2,4-dienoic acid (50 mg) was suspended in NMP:DCP (2 ml, 1:1) for 30 min, then washed with DMF (3×2 ml). The solvent was removed, and a solution of tert-butylaniline (30 mg, 0.2 mmol) in DMF:TMOF (1.5 ml, 1:1) was added followed by HOAc (100 μl). The mixture was stirred at 2 hours at room temperature, before adding a solution of sodium cyanoborohydride (11 mg, 0.15 mmol) in DMF-MeOH (1 ml, 1:1). The mixture was stirred overnight at room temperature, then drained for solvent and washed with DMF (3×2 ml) and DCM (2 ml). A solution of 50% DIPEA in DCM (2 ml) was added and the resin was left stirring for 30 min. The resin was subsequently washed with DCM (3×2 ml), MeOH (1×2 ml) and DCP (2×2 ml).

Workup

  1. washwashed with DMF (3×2 ml)
  2. customThe solvent was removed
  3. stirringThe mixture was stirred overnight at room temperature
  4. washwashed with DMF (3×2 ml) and DCM (2 ml)
  5. additionA solution of 50% DIPEA in DCM (2 ml) was added
  6. waitthe resin was left
  7. stirringstirring for 30 min
  8. washThe resin was subsequently washed with DCM (3×2 ml), MeOH (1×2 ml) and DCP (2×2 ml)

Sources & evidence

ORD record
ord-3813fc6a719946f995060a8819b6da71
Source dataset
uspto-grants-2003_11
Patent number
US06649641B2

Reaction notes

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