Glycine → HCID 178454190, compound

HRID 322551Notes

Reaction equation

HRID 322551 reaction equation
[NH:1]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C@@H:2]([C:30](ON1C(=O)CCC1=O)=[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].[NH2:47][CH2:48][C:49]([OH:51])=[O:50].C([O-])(O)=O.[Na+]>O1CCOCC1.O>[NH:1]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C@@H:2]([C:30]([NH:47][CH2:48][C:49]([OH:51])=[O:50])=[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 3

HCID 750GlycineHCID 516892Sodium BicarbonateHCID 178454192HCID 178454192, compound

Product 1

HCID 178454190HCID 178454190, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of Boc—(D)—Arg(Cbz2)—OSu (1 g, 1.6 mmol) in dioxane (10 mL) was added a solution of Gly (300 mg, 4 mmol) and NaHCO3 (400 mg, 4.76 mmol) in water (10 mL). The solution was stirred for 24 h. Solvents were evaporated and residue was dissolved in a mixture of EtOAc (20 mL) and 1 N HCl (6 mL). The separated organic layer was washed with sat. NaCl (10 mL), dried over MgSO4, filtered and evaporated to give a solid residue which was used directly without further purification. ES—MS (M+H)+=600

Workup

  1. customSolvents were evaporated
  2. dissolutionresidue was dissolved in a mixture of EtOAc (20 mL) and 1 N HCl (6 mL)
  3. washThe separated organic layer was washed with sat. NaCl (10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a solid residue which
  8. customwas used directly without further purification

Sources & evidence

ORD record
ord-3d57bb182271498cb0988d628fb487b4
Source dataset
uspto-grants-2001_04
Patent number
US06211154B1

Reaction notes

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