Water → HCID 53738029, compound

HRID 2380169Notes

Reaction equation

HRID 2380169 reaction equation
[CH3:1][NH:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[C:14]([C:26]1[CH:31]=[CH:30][C:29]([O:32]C)=[CH:28][CH:27]=1)[CH:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=1)[CH2:16][CH3:17].[Br-].[Br-].[Br-].B.O>C(Cl)Cl>[CH3:1][NH:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)=[C:15]([C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=1)[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 54079109HCID 54079109, compoundHCID 178419136HCID 178419136, compound

Product 1

HCID 53738029HCID 53738029, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the above dimethoxy amide 15 (117 mg, 0.22 mmol) in CH2Cl2 (1 ml) at 0° C. was added, under argon, 1.0 M 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, unter 0.063 mm, 30 g). Elution with a mixture of hexane-ethyl acetate (4:1 v/v) gave N-butyl, N-methyl-12,13-Bis (4-hydroxyphenyl)-12-pentadeconic amide ("EM-142", compound 16 with ×=10) (34 mg, 31%), colorless oil, IR νmax (neat) 3300, 1600 cm-1 ; UV νmax (log ε)=235 (4.25) nm; 1H-NMR (δ, CDCl3), 0.76 (3H, t, J= 7.3 Hz, --CH3CH3), 0.96 (3H, t, J=7.3 Hz, N (CH2)3CH3), 2.05-2.20 (4H, m, CH2 -C=C--CH2 --), 2.35 (2H, t, J=7.0 Hz, --CH3CON--), 2.97 and 3.00 (3H, s, --NCH3), 3.29 and 3.41 (2H, 2t, J=7.3 Hz, --N--CH3 --), and 6.59-7.09 (8H, m, H-Ar) ppm; MS m/e=493 (M+). ##STR23##

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, unter 0.063 mm, 30 g)
  6. washElution
  7. additionwith a mixture of hexane-ethyl acetate (4:1 v/v)

Sources & evidence

ORD record
ord-71ddfef831dd4585ae970f6f45b5be51
Source dataset
uspto-grants-1994_11
Patent number
US05364847

Reaction notes

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