Diazomethane → N-[(2S)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propyl]-N-[2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propyl]-N-ethylamine

HRID 402987Notes

Reaction equation

HRID 402987 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:39][C:40]1[CH:45]=[CH:44][C:43]([OH:46])=[CH:42][CH:41]=1)[CH2:10][N:11]([CH2:14][CH:15]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24]C2C=CC=CC=2)=[CH:19][CH:18]=1)[CH2:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+](=[CH2:49])=[N-]>C(OCC)C>[C:35]([O:34][C:32]([NH:31][C@@H:15]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)[CH2:14][N:11]([CH2:10][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([O:46][CH3:49])=[CH:42][CH:41]=1)[CH2:12][CH3:13])=[O:33])([CH3:37])([CH3:36])[CH3:38]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 60204738N-[(2S)-2-(tert-butoxycarbonylamino)-3-[4-(hydroxy)phenyl]propyl]-N-[2-(tert-butoxycarbonylamino)-3-[4-(phenylmethoxy)phenyl]propyl]-N-ethylamine

Product 1

HCID 60204740N-[(2S)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propyl]-N-[2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propyl]-N-ethylamineYield 77%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The product from Example 19A (21 mg, 38 μmol) was treated with diazomethane in diethyl ether (˜0.4 M, 1 mL) at ambient temperature. After stirring for 2 days, the solvent was removed under reduced pressure. The residue was dissolved in fresh diazomethane solution and stirred at ambient temperature for an additional 2 days. This process was repeated until TLC (CHCl3:methanol, 19:1) indicated the reaction was complete. The residue was purified by column chromatography on silica gel (CH2Cl2:methanol, 99:1) to provide the title compound as a colorless amorphous solid (17 mg, 77%). 1H NMR (CDCl3) δ 7.09 (d, J=8.9 Hz, 4H), 6.82 (d, J=8.5 Hz, 4H), 4.70 (br s, 1.3; H), 4.53 (br s, 0.7; H), 3.83-3.78 (m, 2H), 3.78 (s, 6H), 2.85-2.68 (m, 4H), 2.60-2.27 (m, 6H), 1.41 (s, 12H), 1.38 (s, 6H), 0.94-0.84 (m, 3H); MS (APCI+) m/z 572 (M+H)+.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in fresh diazomethane solution
  3. stirringstirred at ambient temperature for an additional 2 days
  4. customThe residue was purified by column chromatography on silica gel (CH2Cl2:methanol, 99:1)

Sources & evidence

ORD record
ord-a7dffcf1cad84c23835dc732c26fd9a4
Source dataset
uspto-grants-2014_06
Patent number
US08741938B2

Reaction notes

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