1,2-Dichloroethane → HCID 86624506, compound

HRID 269663Notes

Reaction equation

HRID 269663 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17][C:18]([OH:20])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:29][CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36].C(N(CC)CC)C.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][CH2:14][CH2:15][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17][C:18]([NH:29][CH2:30][CH2:31][NH:32][C:33]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:39])=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 187201N-BOC-ethylenediamineHCID 2761530HCID 2761530, compound

Product 1

HCID 86624506HCID 86624506, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon, 1 g (2.54 mmol) of (3S)-7-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]heptanoic acid, 406 mg (2.54 mmol) of tert-butyl (2-aminoethyl)carbamate and 0.96 ml of triethylamine (6.85 mmol) are dissolved in 20 ml of dimethylformamide. Then, at 0° C. (ice bath), 826 mg (4.3 mmol) of EDC and 113 mg (0.84 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 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 under high vacuum

Sources & evidence

ORD record
ord-46687f518eb14191980ec13a241c9696
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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