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

HRID 269687Notes

Reaction equation

HRID 269687 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:27]([OH:29])=O)[CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30]([O:34][C:35](=[O:42])[NH:36][CH2:37][CH:38]([OH:41])[CH2:39][NH2:40])([CH3:33])([CH3:32])[CH3:31].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:27]([NH:40][CH2:39][CH:38]([OH:41])[CH2:37][NH:36][C:35]([O:34][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:42])=[O:29])[CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[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 7073470N2,N5-Bis((phenylmethoxy)carbonyl)-L-ornithineHCID 10511887tert-butyl N-(3-amino-2-hydroxypropyl)carbamate

Product 1

HCID 86625290Benzyl {(1S)-4-{[(benzyloxy)carbonyl]amino}-1-[({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)carbonyl]butyl}carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon, 0.20 g (0.50 mmol) of N2,N5-bis[(benzyloxy)carbonyl]-L-ornithine and 0.124 g (0.65 mmol) of tert-butyl(3-amino-2-hydroxypropyl)carbamate are dissolved in 6 ml of dimethylformamide. Then, at 0° C. (ice bath), 0.124 g (0.65 mmol) of EDC and 0.02 g (0.15 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-eb13e90c790d481180c4787dc8e315c8
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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