Citrulline → HCID 131730131, compound

HRID 1797881Notes

Reaction equation

HRID 1797881 reaction equation
[C:1]([N:18]([CH3:33])[C@H:19]([C:23](ON1C(=O)CCC1=O)=[O:24])[CH:20]([CH3:22])[CH3:21])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].[NH2:34][C@H:35]([C:43]([OH:45])=[O:44])[CH2:36][CH2:37][CH2:38][NH:39][C:40]([NH2:42])=[O:41].C([O-])(O)=O.[Na+]>COCCOC.C1COCC1.O>[C:1]([N:18]([CH3:33])[C@H:19]([C:23]([NH:34][C@H:35]([C:43]([OH:45])=[O:44])[CH2:36][CH2:37][CH2:38][NH:39][C:40]([NH2:42])=[O:41])=[O:24])[CH:20]([CH3:21])[CH3:22])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2]

Participants

7

Reactant 3

HCID 9750CitrullineHCID 516892Sodium BicarbonateHCID 131730132N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-valine 2,5-dioxo-1-pyrrolidinyl ester

Product 1

HCID 131730131HCID 131730131, compoundYield 81.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a room temperature suspension of Fmoc-MeVal-OSu (2.18 g, 4.84 mmol) in DME (13 mL) and THF (6.5 mL) is added a solution of L-citrulline (0.85 g, 4.84 mmol) and NaHCO3 (0.41 g, 4.84 mmol) in H2O (13 mL). The suspension is allowed to stir at room temperature for 16 hr, then it is extracted into tert-BuOH/CHCl3/H2O and acidified to pH=2-3 with 1 M HCl. The organic phase is separated, dried and concentrated under reduced pressure. The residue is triturated with diethyl ether resulting Fmoc-MeVal-Cit-COOH (e.g., 2.01 g) which is used without further purification.

Workup

  1. extractionit is extracted into tert-BuOH/CHCl3/H2O
  2. customThe organic phase is separated
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is triturated with diethyl ether

Sources & evidence

ORD record
ord-245117e4a2324fe4b9dadbccc2581d75
Source dataset
uspto-grants-2013_01
Patent number
US08343928B2

Reaction notes

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