4-Pentylaniline → HCID 67396887, compound

HRID 914514Notes

Reaction equation

HRID 914514 reaction equation
[C:1]([CH2:4][C:5]1[N:6]=[C:7]([S:10][C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13])[S:8][CH:9]=1)(O)=O.[CH2:17]([C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1)[CH2:18][CH2:19][CH2:20][CH3:21]>O1CCCC1>[CH3:15][C:11]([S:10][C:7]1[S:8][CH:9]=[C:5]([CH2:4][CH2:1][NH:26][C:25]2[CH:27]=[CH:28][C:22]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:23][CH:24]=2)[N:6]=1)([CH3:16])[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 931624-PentylanilineHCID 67399201HCID 67399201, compound

Product 1

HCID 67396887HCID 67396887, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An operation similar to that of Example 520-1 was performed using 2-{[4-(carboxymethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid resin synthesized in Example 461-4 and 4-amylaniline (0.098 g) as starting materials. To the obtained resin were added tetrahydrofuran (2.0 mL) and 1 mol/L borane-tetrahydrofuran complex (2.0 mL), and the mixture was stirred at room temperature overnight. The resin was collected by filtration from the reaction mixture, washed once with tetrahydrofuran, twice with tetrahydrofuran/methanol=1:1 solution, and twice with methanol. Then, a solution (4.0 mL) of tetrahydrofuran-methanol-piperidine (1:1:2) was added to the resin, and the mixture was stirred at room temperature overnight. After completion of the reaction, the resin was collected by filtration, washed four times with tetrahydrofuran and twice with methanol, and vacuum dried to give the title pale-yellow resin (0.30 g).

Workup

  1. filtrationThe resin was collected by filtration from the reaction mixture
  2. washwashed once with tetrahydrofuran, twice with tetrahydrofuran/methanol=1:1 solution
  3. additionThen, a solution (4.0 mL) of tetrahydrofuran-methanol-piperidine (1:1:2) was added to the resin
  4. stirringthe mixture was stirred at room temperature overnight
  5. customAfter completion of the reaction
  6. filtrationthe resin was collected by filtration
  7. washwashed four times with tetrahydrofuran
  8. dry with materialtwice with methanol, and vacuum dried

Sources & evidence

ORD record
ord-0d9b47ecf33d4e9a96e7fafa3c408767
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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