1,2-Dichloroethane → HCID 14805851, compound

HRID 900568Notes

Reaction equation

HRID 900568 reaction equation
[C:1]([O:5][C:6](=[O:12])[C@@H:7]1[CH2:11][CH2:10][CH2:9][NH:8]1)([CH3:4])([CH3:3])[CH3:2].[C:13]([NH:23][C:24]([CH3:29])([C:26](O)=[O:27])[CH3:25])([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[C:1]([O:5][C:6]([CH:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:26](=[O:27])[C:24]([NH:23][C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])([CH3:29])[CH3:25])=[O:12])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 294936N-((Benzyloxy)carbonyl)-2-methylalanineHCID 6453108L-Proline 1,1-dimethylethyl ester

Product 1

HCID 14805851HCID 14805851, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of proline-tert-butyl ester (47) (2.00 g, 12 mmol, in CH2Cl2 (15 ml) was added N-carbobenzyloxy-2-methylalanine (3.05 g, 13 mmol), HOBT (2.36 g, 17 mmol) and EDC (3.43 g, 18 mmol) and the solution was stirred at room temperature under N2 for 48 hours. The solvent was evaporated, the crude material dissolved in EtOAc and washed with 0.5N NaHSO4 (2×), saturated NaHCO3 (2×) and brine and was dried over anhydrous Na2SO4, filtered and evaporated to give a white solid (4.68 g, 100%). 1H-NMR (500 MHz, CDCl3) δ 1.20-2.15 (m, 4H), 1.43 (s, 9H), 1.59 (d, 6H), 3.21-3.79 (m, 2H), 4.35 (br s, 1H), 4.82-5.19 (m, 3H), 5.74 (br s, 1H), 7.17-7.49 (m, 5H). Analytical HPLC (C18 column) 10.66 min. LC-MS (ES+) m/e=391.3 (M+H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude material dissolved in EtOAc
  3. washwashed with 0.5N NaHSO4 (2×), saturated NaHCO3 (2×) and brine
  4. dry with materialwas dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4c157910169342c1b36d2ec6bdac59ad
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

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