Triethylamine → HCID 86612119, compound

HRID 2114841Notes

Reaction equation

HRID 2114841 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:4]=1[CH2:5][NH:6][CH2:7][C:8]1([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:12][CH2:11][CH2:10][CH2:9]1.CCN(CC)CC.[Br:34][CH2:35][C:36](Br)=[O:37]>C1COCC1>[Br:34][CH2:35][C:36]([N:6]([CH2:7][C:8]1([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][CH2:10][CH2:11][CH2:12]1)[CH2:5][C:4]1[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:3]=1[O:2][CH3:1])=[O:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 69317052HCID 69317052, compound

Product 1

HCID 86612119HCID 86612119, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 1-{[(2,4-dimethoxybenzyl)amino]methyl}cyclopentyl-carbamate (3.20 g, 8.78 mmol) in anhydrous THF (25 mL) was added Et3N (1.35 mL, 9.65 mmol). The solution was cooled to 0° C., treated with bromoacetyl bromide (0.84 mL, 9.65 mmol), and stirred for 3 h. The reaction was poured into ice water and extracted three times into Et2O. The combined organics were dried over Na2SO4, filtered, and concentrated in vacuo. The resulting crude material was subjected to column chromatography eluting with a gradient of 0-100% EtOAc/hexanes. Collection and concentration of the appropriate fractions afforded the product.

Workup

  1. extractionextracted three times into Et2O
  2. dry with materialThe combined organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washeluting with a gradient of 0-100% EtOAc/hexanes
  6. customCollection and concentration of the appropriate fractions
  7. customafforded the product

Sources & evidence

ORD record
ord-27923f49efd54f78a537f04a4fd1d1a2
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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