Water → HCID 66679455, compound

HRID 1183805Notes

Reaction equation

HRID 1183805 reaction equation
[CH2:1]([O:8][C:9](=[O:30])[N:10]([CH2:26][CH2:27][CH2:28][NH2:29])[CH2:11][CH2:12][CH2:13][CH:14]([NH2:25])C(OCC1C=CC=CC=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:36][CH3:37])CC)C.Br[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41].[OH2:45]>C(#N)C>[CH2:43]([O:42][C:40](=[O:41])[CH2:39][NH:29][CH2:28][CH2:27][CH2:26][N:10]([C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:30])[CH2:11][CH2:12][CH2:13][CH2:14][NH:25][C:1]([O:8][CH2:9][C:37]1[CH:36]=[CH:4][CH:3]=[CH:2][CH:7]=1)=[O:45])[CH3:44]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 66680028HCID 66680028, compound

Product 1

HCID 66679455HCID 66679455, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6.35 g (15.4 mmol) of (3-aminopropyl)-(4-benzyloxycarbonyl-aminobutyl)-carbamic acid benzyl ester (Synth. Commun. 2005, 35, 1085) in 200 mL of acetonitrile, and 2.6 mL (1.86 g, 15.4 mmol) of triethylamine, there are introduced, with stirring, at ambient temperature, 1.70 mL (2.56 g, 15.4 mmol) of ethyl bromoacetate. Stirring is maintained for 4 hours. The reaction mixture is poured into water and extracted with ethyl acetate. The organic phases are separated off and then dried over sodium sulfate, filtered and evaporated. 7.7 g of an oil are obtained, which is used directly in the following step.

Workup

  1. stirringStirring
  2. temperatureis maintained for 4 hours
  3. extractionextracted with ethyl acetate
  4. customThe organic phases are separated off
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-468f6992bafc49b082090652232da049
Source dataset
uspto-grants-2014_03
Patent number
US08664409B2

Reaction notes

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