Triethylamine → HCID 178501235, compound

HRID 732707Notes

Reaction equation

HRID 732707 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8](C(O)=O)[CH2:7][CH2:6]1)=[O:4].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:21])=CC=1.[C:31]1([C@H:41]([N:43]([CH2:51][C@@H:52]2[C@@H:56]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[CH2:55][NH:54][CH2:53]2)[C:44](=[O:50])[O:45][C:46]([CH3:49])([CH3:48])[CH3:47])[CH3:42])[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1.C([N:65]([CH2:68]C)CC)C>C1(C)C=CC=CC=1>[C:46]([O:45][C:44]([N:43]([CH2:51][C@@H:52]1[C@@H:56]([C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[CH2:55][N:54]([C:68]([NH:65][C@H:8]2[CH2:7][CH2:6][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:9]2)=[O:21])[CH2:53]1)[C@@H:41]([C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1)[CH3:42])=[O:50])([CH3:48])([CH3:49])[CH3:47]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 86628525tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamateHCID 178501163HCID 178501163, compound

Product 1

HCID 178501235HCID 178501235, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 144 mg of trans-1,4-cyclohexanedicarboxylic acid monomethyl ester, 213 mg of DPPA and 6 ml of toluene was mixed with 157 mg of triethylamine at room temperature and stirred at 80° C. for 3Hours. The reaction solution was spontaneously cooled down to room temperature, and a 2 ml toluene solution of 332 mg of tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamate was added thereto and stirred overnight at room temperature. The reaction solution was washed with 1 M hydrochloric acid, water and 1 M sodium hydroxide aqueous solution in that order and dried with anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure, and the residue was purified by a silica gel column chromatography (chloroform-methanol) to obtain 336 mg of methyl trans-4-({[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}amino)cyclohexane-carboxylate as a colorless amorphous substance.

Workup

  1. temperatureThe reaction solution was spontaneously cooled down to room temperature
  2. stirringstirred overnight at room temperature
  3. washThe reaction solution was washed with 1 M hydrochloric acid, water and 1 M sodium hydroxide aqueous solution in that order
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was evaporated under a reduced pressure
  6. customthe residue was purified by a silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-8cf9da949fca424294c8a833a8c3b451
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

Loading…