Water → HCID 53704459, compound

HRID 357325Notes

Reaction equation

HRID 357325 reaction equation
[CH2:1]([N:5]([CH3:38])[C:6](=[O:37])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[C:17]([C:29]1[CH:34]=[CH:33][C:32]([O:35]C)=[CH:31][CH:30]=1)[CH:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=1)[CH2:19][CH3:20])[CH2:2][CH2:3][CH3:4].[Br-].[Br-].[Br-].B.O>C(Cl)Cl>[CH2:1]([N:5]([CH3:38])[C:6](=[O:37])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)=[C:18]([C:21]1[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=1)[CH2:19][CH3:20])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 54103883HCID 54103883, compoundHCID 178419136HCID 178419136, compound

Product 1

HCID 53704459HCID 53704459, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the above dimethoxy amide 4 (117 mg, 0.22 mmol) in CH2Cl2 (1 ml) at 0° C. was added, under argon, 1.0M borane tribromide (675 μl). The solution was stirred for 1 hour, then poured into water and extracted with ether (3×). The organic solution was washed with water, dried on magnesium sulfate, and evaporated to dryness. The residue was purified by "Flash chromatography" on silica gel (Kieselgel 60, Merck, under 0.063 mm, 30 g). Elution with mixture of hexane-ethyl acetate (4:1 v/v) gave N-butyl,N-methyl-12,13-Bis(4-hydroxyphenyl)-12-pentadecenoic amide (EM-142, compound 5 with x=10) (34 mg, 31%), colorless oil, IR νmax (neat) 3300, 1600 cm-1 ; UV γmax (log ε)=235 (4.25) nm; 1H-NMR (δ, CDCl3), 0.76 (3H, t, J=7.3 Hz, --C2CHH3), 0.96 (3H, t, J=7.3 Hz, N(CH2)3 CH3), 2.05-2.20 (4H, m, CH2 --C=C--C2 --), 2.35 (2H, t, J=7.0 Hz, --CH2CON--), 2.97 and 3.00 (3H, s, --NCH3), 3.29 and 3.41 (2H, 2t, J=7.3 Hz, --N--CH2 --), and 6.59-7.09 (8H, m, H--Ar) ppm; MS m/e=493 (M+). ##STR74##

Workup

  1. extractionextracted with ether (3×)
  2. washThe organic solution was washed with water
  3. customdried on magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by "Flash chromatography" on silica gel (Kieselgel 60, Merck, under 0.063 mm, 30 g)
  6. washElution
  7. additionwith mixture of hexane-ethyl acetate (4:1 v/v)

Sources & evidence

ORD record
ord-bd9e55800b2347fe8bea0b58d1fa2c3c
Source dataset
uspto-grants-1998_11
Patent number
US05840735

Reaction notes

Loading…