Triethylamine → HCID 68433262, compound

HRID 1162845Notes

Reaction equation

HRID 1162845 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[CH2:6]([O:13][CH2:14][CH:15]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:16][NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C1COCC1>[CH2:6]([O:13][CH2:14][CH:15]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])[CH2:16][N:17]([C:3](=[O:4])[CH2:2][Br:1])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 68432621HCID 68432621, compound

Product 1

HCID 68433262HCID 68433262, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Bromoacetyl bromide (588 μL, 6.75 mmol) was added slowly to a stirred solution of tert-butyl 2-(benzyloxy)-1-{[(4-fluorobenzyl)amino]-methyl}ethylcarbamate (2.39 g, 6.14 mmol) and triethylamine (941 μL, 6.75 mmol) in anhydrous THF (12 mL) at 0° C. under inert atmosphere. After stirring for 20 min, the reaction was poured into ice water and extracted twice with diethyl ether. The combined organic layers were washed twice with brine, dried over Na2SO4, and concentrated in vacuo. The resulting orange/brown oil was purified by silica gel chromatography (10% to 40% EtOAc/hexanes) to afford the title compound as a red-orange oil. 1H NMR (500 MHz, CDCl3) δ 7.40-7.21 (m, 6H), 7.16-6.96 (m, 3H), 5.20 (d, J=8.0 Hz, 1H), 5.01 (d, J=9.0 Hz, 1H), 4.75-4.66 (m, 1H), 4.59-4.48 (m, 2H), 4.39 (d, J=15.0 Hz, 1H), 4.04-3.92 (m, 2H), 3.87-3.28 (m, 4H), 1.43 (s, 9H). ES MS (M+1−100, for loss of BOC group)=409.4.

Workup

  1. extractionextracted twice with diethyl ether
  2. washThe combined organic layers were washed twice with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting orange/brown oil was purified by silica gel chromatography (10% to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-735e4d0bf17546dd99dcde539d706af4
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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