1,2-Dichloroethane → Benzyl {(4S)-6-({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-4-[(tert-butoxycarbonyl)amino]-6-oxohexyl}carbamate

HRID 269666Notes

Reaction equation

HRID 269666 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@H:15]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][C:17]([OH:19])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]([O:32][C:33](=[O:49])[NH:34][CH2:35][CH2:36][CH2:37][C@H:38]([NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:39][NH2:40])([CH3:31])([CH3:30])[CH3:29].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][C@H:15]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][C:17]([NH:40][CH2:39][C@@H:38]([NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:37][CH2:36][CH2:35][NH:34][C:33]([O:32][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:49])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 16105711(3S)-6-{[(benzyloxy)carbonyl]amino}-3-{[(tert-butoxy)carbonyl]amino}hexanoic acidHCID 57440197tert-Butyl {(4S)-5-amino-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate

Product 1

HCID 86624517Benzyl {(4S)-6-({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-4-[(tert-butoxycarbonyl)amino]-6-oxohexyl}carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon, 0.1 g (0.263 mmol) of (3S)-6-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]hexanoic acid (Bioorg. Med. Chem. Lett. (1998) 8:1477-1482) and 0.108 g (0.342 mmol) of tert-butyl{(4S)-5-amino-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate (Example 86A) are dissolved in 6 ml of dimethylformamide. Then, at 0° C. (ice bath), 0.066 g (0.342 mmol) of EDC and 0.011 g (0.079 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-1874c7a26e14428ea290244773b7d6e3
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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