Triethylamine → HCID 15231959, compound

HRID 274807Notes

Reaction equation

HRID 274807 reaction equation
[C:1]12(C(O)=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.P(N=[N+]=[N-])(N=[N+]=[N-])(N=[N+]=[N-])=[O:15].C([N:27]([CH2:30]C)CC)C.[NH2:32][CH:33]([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[CH:34]([NH:41][C:42]([NH:44][C:45]1[CH:50]=[CH:49][C:48]([C:51]([F:54])([F:53])[F:52])=[CH:47][CH:46]=1)=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1(C)C=CC=CC=1>[C:35]1([CH:34]([NH:41][C:42]([NH:44][C:45]2[CH:50]=[CH:49][C:48]([C:51]([F:52])([F:53])[F:54])=[CH:47][CH:46]=2)=[O:43])[CH:33]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[NH:32][C:30]([NH:27][C:1]23[CH2:2][CH:3]4[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]4)[CH2:8]2)[CH2:10]3)=[O:15])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 132351-Adamantanecarboxylic acidHCID 15231944HCID 15231944, compoundHCID 18425119HCID 18425119, compound

Product 1

HCID 15231959HCID 15231959, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-adamantyl carboxylic acid (0.04 g, 0.21 mmol) in dry toluene (5 mL) is added phosphoryl azide (0.06 g, 0.21 mmol) and triethyl amine (0.02 g, 0.21 mmol). The resulting mixture is heated to reflux for 4 hours. [R--(R*,R*)] and [S--(R*,R*)]-N-(2-amino-1,2-diphenylethyl)-N'-[4-(trifluoromethyl)-phenyl]urea (0.1 g, 0.25 mmol) is then added and the mixture is allowed to cool to room temperature. The solution is concentrated in vacuo and the residue dissolved in CH2Cl2 and washed with aqueous 1N NaOH, saturated aqueous NaCl, and dried over MgSO4. Filtration and concentration provides an oil which is purified by flash chromatography (SiO2, EtOAc/hexane eluent). The solid product is triturated in diethyl ether and filtered to provide 0.06 g (48%) of a white solid, mp 236°-237° C. NMR (DMSO-d6): 1.47-1.92 (m, 15H), 4.89 (m, 2H), 5.74 (s, 1H), 6.35 (d, 1H, J=7.8 Hz), 6.90-7.21 (m, 11H), 7.56 (m, 4H), 9.13 (s, 1H). Analysis calculated for C33H35F3N4O2.0.2H2O: C, 68.20; H, 6.16; N, 9.64. Found: C, 68.22; H, 6.16; N, 9.53.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux for 4 hours
  3. concentrationThe solution is concentrated in vacuo
  4. dissolutionthe residue dissolved in CH2Cl2
  5. washwashed with aqueous 1N NaOH, saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. filtrationFiltration and concentration
  8. customprovides an oil which
  9. customis purified by flash chromatography (SiO2, EtOAc/hexane eluent)
  10. customThe solid product is triturated in diethyl ether
  11. filtrationfiltered

Sources & evidence

ORD record
ord-3d4fcb49d2da489f85542eef7e427900
Source dataset
uspto-grants-1995_02
Patent number
US05389682

Reaction notes

Loading…