Citric Acid → HCID 59841868, compound

HRID 1946233Notes

Reaction equation

HRID 1946233 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH2:9])=[O:8].C(=O)(O)[O-].[Na+].[NH:18]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C@H:19]([C:23](ON1C(=O)CCC1=O)=[O:24])[CH:20]([CH3:22])[CH3:21].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.C(COC)OC.O1CCCC1>[NH:18]([C:33]([O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[O:34])[C@H:19]([C:23]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH2:9])=[O:8])=[O:24])[CH:20]([CH3:21])[CH3:22]

Participants

8

Reactant 4

HCID 311Citric AcidHCID 9750CitrullineHCID 98768Boc-Val-osuHCID 516892Sodium Bicarbonate

Product 1

HCID 59841868HCID 59841868, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of Citrulline (2.54 g, 14.50 mmole) and Sodium Bicarbonate (1.28 g) in water (40 mL) was added Boc-Val-OSu (4.34 g, 13.81 mmole) dissolved in dimethoxyethane (DME). To aid the solubility of the mixture tetrahydrofuran (10 mL) was added. The mixture thus obtained was let stir overnight at room temperature. Aqueous citric acid (15%, 75 mL) was added and the mixture was extracted with 10% 2-propanol/ethyl acetate (2×100 mL). The organic layer was washed with brine (2×150 mL) and the solvents were removed on the rotovap. The resulting white solid was dried in vacuo for 5 hours and then treated with ether (100 mL). After brief sonication and trituration, the white solid product was collected by filtration (1.39 g, 27%). 1H NMR (CD3OD) δ 0.91 (dd, 3H), 0.98 (dd, 3H), 1.44 (s, 9H), 1.70 (m, 2H), 1.87 (m, 2H), 2.02 (m, 2H), 3.11 (t, 2H), 3.89 (t, 1H), 4.39 (q, 1H), 8.22 (d, 1H) ppm; LC-MS (ESI) 375 (M+H+).

Workup

  1. additionwas added
  2. customThe mixture thus obtained
  3. extractionthe mixture was extracted with 10% 2-propanol/ethyl acetate (2×100 mL)
  4. washThe organic layer was washed with brine (2×150 mL)
  5. customthe solvents were removed on the rotovap
  6. customThe resulting white solid was dried in vacuo for 5 hours
  7. additiontreated with ether (100 mL)
  8. customAfter brief sonication and trituration
  9. filtrationthe white solid product was collected by filtration (1.39 g, 27%)

Sources & evidence

ORD record
ord-06d40b6e431446f79da2c4e3c569def0
Source dataset
uspto-grants-2013_03
Patent number
US08399403B2

Reaction notes

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