Ethyl Acetate → HCID 178471825, compound

HRID 1770670Notes

Reaction equation

HRID 1770670 reaction equation
[NH2:1][C@H:2]([C:16]([O:18]CCN(CC)CC)=[O:17])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:15])[N:8]([C:12]([CH3:14])=[O:13])[C:9]([CH3:11])=[O:10].[NH:26](C(OC(C)(C)C)=O)[C@H:27]([C:34]([N:36]1[CH2:50][CH2:49][CH2:48][C@H:37]1[C:38](ON1C(=O)CCC1=O)=[O:39])=[O:35])[CH2:28][C:29](=[O:33])[O:30][CH2:31][CH3:32].C(OCC)(=O)C>C([O-])(O)=O.[Na+].CC(C)=O>[NH2:26][C@H:27]([C:34]([N:36]1[CH2:50][CH2:49][CH2:48][C@H:37]1[C:38]([NH:1][C@H:2]([C:16]([OH:18])=[O:17])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:15])[N:8]([C:9]([CH3:11])=[O:10])[C:12]([CH3:14])=[O:13])=[O:39])=[O:35])[CH2:28][C:29](=[O:33])[O:30][CH2:31][CH3:32]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 131734633HCID 131734633, compoundHCID 178464106HCID 178464106, compound

Product 1

HCID 178471825HCID 178471825, compoundYield 121.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

22 g of H-Arg(diAc)-OCH2CH2N(CH2CH3)2 was dissolved in 300 ml of 5% NaHCO3. 24 g of Boc-Asp(OEt)-Pro-OSu in 150 ml of acetone was added into the reaction mixture. The mixture was stirred for 5 h at RT. 500 ml of ethyl acetate was added into the mixture. The ethyl acetate solution was washed with water (3×100 ml). The organic solution was dried over sodium sulfate. The solution was evaporated to dryness. The residue was dissolved in 250 ml of dichloromethylene. 200 ml of trifluoroacetic acid was added into the mixture and the mixture was stirred for 30 min. The mixture was evaporated to dryness to yield 32 g of H-Asp(OEt)-Pro-Arg(diAc)*OCH2CH2N(CH2CH3)2.2TFA.

Workup

  1. washThe ethyl acetate solution was washed with water (3×100 ml)
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. customThe solution was evaporated to dryness
  4. dissolutionThe residue was dissolved in 250 ml of dichloromethylene
  5. addition200 ml of trifluoroacetic acid was added into the mixture
  6. stirringthe mixture was stirred for 30 min
  7. customThe mixture was evaporated to dryness

Sources & evidence

ORD record
ord-90eae7552fdf4892badd0f832a68a13b
Source dataset
uspto-grants-2016_02
Patent number
US09248109B2

Reaction notes

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