Triethylamine → HCID 91114335, compound

HRID 574807Notes

Reaction equation

HRID 574807 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][C@H:4]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1.Br[CH2:19][CH2:20][O:21][CH2:22][CH2:23]Br.C(N(CC)CC)C.C(OCC)(=O)C>CN(C)C=O>[O:21]1[CH2:22][CH2:23][N:1]([C@@H:2]2[CH2:6][CH2:5][C@H:4]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:3]2)[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 21521Bis(2-bromoethyl) etherHCID 86619697Benzyl ((1S,3R)-3-aminocyclopentyl)carbamate

Product 1

HCID 91114335HCID 91114335, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of EXAMPLE 111B (400 mg), 1-bromo-2-(2-bromoethoxy)ethane (0.246 mL), and triethylamine (0.595 mL) in N,N-dimethylformamide (6 mL) was stirred at 70° C. for 24 hours. The solution was cooled and poured into ethyl acetate (200 mL). The solution was extracted with 3× water, washed with brine, concentrated, and chromatographed on silica gel using 10% methanol/ethyl acetate to give the pure product.

Workup

  1. temperatureThe solution was cooled
  2. extractionThe solution was extracted with 3× water
  3. washwashed with brine
  4. concentrationconcentrated
  5. customchromatographed on silica gel using 10% methanol/ethyl acetate
  6. customto give the pure product

Sources & evidence

ORD record
ord-027c7a222a084dc49279e776394e79c2
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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