Isobutylamine → HCID 20157325, compound

HRID 986374Notes

Reaction equation

HRID 986374 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]/[CH:16]=[CH:17]/[C:18]([OH:20])=O.C(N(CC)CC)C.C1(NP(Cl)(=O)OC2C=CC=CC=2)C=CC=CC=1.[CH2:50]([NH2:54])[CH:51]([CH3:53])[CH3:52]>ClCCl>[CH2:50]([NH:54][C:18](=[O:20])/[CH:17]=[CH:16]/[CH:15]=[CH:14]/[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][CH2:6][C:5]1[CH:21]=[CH:22][CH:23]=[C:3]([C:2]([F:1])([F:25])[F:24])[CH:4]=1)[CH:51]([CH3:53])[CH3:52]

Participants

6

Reactant 4

HCID 6558IsobutylamineHCID 8471Triethylamine2×HCID 103959Phosphoramidochloridic acid, N-phenyl-, phenyl esterHCID 20157319HCID 20157319, compound

Product 1

HCID 20157325HCID 20157325, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step (d) (1 g, 2.8 mmol) was treated with triethylamine (0.66 mL, 4.8 mmol) and phenyl N-phenylphosphoroamidochloridate (1 g, 3.8 mmol) in dry dichloromethane for 30 mins under nitrogen at room temperature. Isobutylamine (0.66 mL, 6.6 mmol) and triethylamine (0.66 mL, 4.8 mmol) were added and after 24 hours the reaction mixture was subjected to standard work-up procedures. The crude product was purified by column chromatography (1:1 hexane:ether, silica) to give 0.57 g (50% of theory) of N-isobutyl 11-(3'trifluoromethylbenzyloxy)-(2E,4E)-undecadienamide. mp 48°-50°.

Workup

  1. customThe crude product was purified by column chromatography (1:1 hexane:ether, silica)

Sources & evidence

ORD record
ord-9e3be35748e5409eaddc093b46001026
Source dataset
uspto-grants-1987_12
Patent number
US04713200

Reaction notes

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