1,2-Dichloroethane → Benzyl{(1S)-4-[(tert-butoxycarbonyl)amino]-1-[({(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutyl}amino)carbonyl]butyl}carbamate

HRID 269672Notes

Reaction equation

HRID 269672 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([OH:26])=O)[CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)[NH:36][CH2:37][CH2:38][C@H:39]([NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:40][OH:41])C1C=CC=CC=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C@H:12]([C:24]([NH:36][CH2:37][CH2:38][C@H:39]([NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:40][OH:41])=[O:26])[CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 7350734Z-Ndelta-Boc-L-ornithineHCID 59722512Boc-Dab(Z)-Ol (S)

Product 1

HCID 131727168Benzyl{(1S)-4-[(tert-butoxycarbonyl)amino]-1-[({(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutyl}amino)carbonyl]butyl}carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon, 0.082 g (0.22 mmol) of N2-[(benzyloxy)carbonyl]-N5-(tert-butoxycarbonyl)-L-ornithine and 0.059 g (0.29 mmol) of benzyl{(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutyl}carbamate (Example 237A) are dissolved in 6 ml of dimethylformamide. Then, at 0° C. (ice bath), 0.056 g (0.29 mmol) of EDC and 0.009 g (0.067 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-ef59c8dc4b8c4c36b56bef2e239fbb32
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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