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1,2-Dichloroethane → Benzyl[3-({2-[(tert-butoxycarbonyl)amino]ethyl}amino)-3-oxopropyl]carbamate

HRID 269683
Notes
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Reaction equation

HRID 269683 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:21][C:22](=[O:27])[NH:23][CH2:24][CH2:25][NH2:26])([CH3:20])([CH3:19])[CH3:18].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:10])[NH:11][CH2:12][CH2:13][C:14]([NH:26][CH2:25][CH2:24][NH:23][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:27])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 75313N-Benzyloxycarbonyl-beta-alanineHCID 757711-HydroxybenzotriazoleHCID 187201N-BOC-ethylenediamine

Product 1

HCID 69493637Benzyl[3-({2-[(tert-butoxycarbonyl)amino]ethyl}amino)-3-oxopropyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

Under argon, 0.20 g (0.90 mmol) of N-[(benzyloxy)carbonyl]-beta-alanine and 0.187 g (1.17 mmol) of tert-butyl(2-aminoethyl)carbamate are dissolved in 6 ml of dimethylformamide. Then, at 0° C. (ice bath), 0.223 g (1.17 mmol) of EDC and 0.036 g (0.27 mmol) of HOBt are added. The mixture is slowly warmed to RT and stirred at RT for 12 h. The solution is concentrated in vacuo and the residue is taken up with ethyl acetate. The organic phase is washed successively with saturated sodium bicarbonate and sodium chloride solutions, dried over magnesium sulfate and evaporated in vacuo. The remaining solid is dried to constant weight under high vacuum.

Workup

  1. concentrationThe solution is concentrated in vacuo
  2. washThe organic phase is washed successively with saturated sodium bicarbonate and sodium chloride solutions
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe remaining solid is dried to constant weight under high vacuum

Sources & evidence

ORD record
ord-71e51ccd21414cc6a4ea4b7a91ce55fd
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07446102B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes