1,2-Dichloroethane → HCID 178454192, compound

HRID 1531257Notes

Reaction equation

HRID 1531257 reaction equation
[NH:1]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C@@H:2]([C:30]([OH:32])=[O:31])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:29])[N:8]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].O[N:41]1[C:46](=[O:47])[CH2:45][CH2:44][C:42]1=[O:43].CCN(C(C)C)C(C)C.C(Cl)CCl>C(Cl)Cl>[NH:1]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C@@H:2]([C:30]([O:32][N:41]1[C:46](=[O:47])[CH2:45][CH2:44][C:42]1=[O:43])=[O:31])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:29])[N:8]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 80170N-HydroxysuccinimideHCID 81531DiisopropylethylamineHCID 178454191HCID 178454191, compound

Product 1

HCID 178454192HCID 178454192, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Boc-(D)-Arg(Cbz2)—OH (1 g, 1.8 mmol) in CH2Cl2 (10 mL) was added HOSu (466 mg, 4.06 mmol), DIEA (1 mL) and EDC (846 mg, 4.4 mmol). The solution was stirred for 48 h. The solvent was evaporated and residue was dissolved in EtOAc (50 mL) and water (10 mL). The separated organic layer was washed with sat. NaHCO3 (10 mL), water (10 mL), 1 M HCl (10 mL) and sat. NaCl (3×10 mL). The organic layer was dried over MgSO4, filtered and evaporated. The oily residue was either used directly in Example 4 without further purification or purified by flash column over silica gel (50% EtOAc in hexane) to give Boc-(D)-Arg(Cbz2)-OSu (1 g, 85% yield).

Workup

  1. customThe solvent was evaporated
  2. dissolutionresidue was dissolved in EtOAc (50 mL)
  3. washThe separated organic layer was washed with sat. NaHCO3 (10 mL), water (10 mL), 1 M HCl (10 mL) and sat. NaCl (3×10 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe oily residue was either used directly in Example 4 without further purification
  8. custompurified by flash column over silica gel (50% EtOAc in hexane)

Sources & evidence

ORD record
ord-6d73cca7cf0c4a4f96dd6cdf9f50e014
Source dataset
uspto-grants-2001_03
Patent number
US06197748B1

Reaction notes

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