1,2-Dichloroethane → HCID 19364751, compound

HRID 900571Notes

Reaction equation

HRID 900571 reaction equation
[CH2:1]1[CH2:5][NH:4][C@H:3]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:2]1.Cl.CCN(C(C)C)C(C)C.[NH:26]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C@H:27]([C:32](O)=[O:33])[C:28]([CH3:31])([CH3:30])[CH3:29].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl.CCOC(C)=O>[CH2:9]([O:8][C:6]([CH:3]1[CH2:2][CH2:1][CH2:5][N:4]1[C:32](=[O:33])[CH:27]([NH:26][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:28]([CH3:31])([CH3:30])[CH3:29])=[O:7])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733413Proline benzyl ester hydrochlorideHCID 2734668(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid

Product 1

HCID 19364751HCID 19364751, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of H-pro-OBzl.HCl (2.00 g, 8.66 mmol) in CH2Cl2 (20 ml) was added DIEA (2.25 ml, 12.92 mmol) to give a colorless solution. Boc-tLeu-OH (1.95 g, 9.52 mmol), HOBT (1.76 g, 13.03 mmol) and EDC (2.49 g, 12.95 mmol) were added and the solution stirred under N2 at room temperature for 18 hours. Removed solvent in vacuo, dissolved in EtOAc and washed with H2O, 0.5N NaHSO4 (2×), saturated NaHCO3 (2×) and brine. Dried over anhydrous Na2SO4 and evaporated to give the title compound. (3.57 g, 99% yield). 1H-NMR (500 MHz, CDCl3) δ 0.99 (s, 9H), 1.40 (s, 9H), 1.88-2.33 (m, 4H), 3.58-3.90 (m, 2H), 4.21-4.35 (d, 1H), 4.53-4.66 (m, 1H), 5.04-5.38 (m, 3H), 7.14-7.42 (m, 5H). LC-MS (ES+) m/e=419.4 (M+H).

Workup

  1. customto give a colorless solution
  2. washwashed with H2O, 0.5N NaHSO4 (2×), saturated NaHCO3 (2×) and brine
  3. dry with materialDried over anhydrous Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-56e806d4d7e14537847e29fdd475fa09
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

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