Citric Acid → Boc-Lys(Z)-Leu-Leu-OH

HRID 1513533Notes

Reaction equation

HRID 1513533 reaction equation
[NH:1]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C@H:2]([C:18]([NH:20][C@H:21]([C:26]([NH:28][C@H:29]([C:34]([O:36]C)=[O:35])[CH2:30][CH:31]([CH3:33])[CH3:32])=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CC(C)=O.O>[NH:1]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C@H:2]([C:18]([NH:20][C@H:21]([C:26]([NH:28][C@H:29]([C:34]([OH:36])=[O:35])[CH2:30][CH:31]([CH3:32])[CH3:33])=[O:27])[CH2:22][CH:23]([CH3:24])[CH3:25])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 12020545HCID 12020545, compound

Product 1

HCID 12020555Boc-Lys(Z)-Leu-Leu-OH

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

Boc-Lys(Z)-Leu-Leu-OMe (12.0 g, 19.33 mmol) was dissolved in acetone (41.0 g, 52 mL) at 22-23° C. A solution of NaOH (1.94 g, 48.5 mmol) in water (18.0 g) was added over 5 min. After stirring for 40 min., the reaction was quenched with a solution of citric acid (10.2 g, 53.0 mmol) in water (18.0 g). The acetone was removed on a rotary evaporator at 40° C. The remaining mixture was extracted with ethyl acetate (2×65 mL). The EtOAc extract was washed with water (50 g) then with aqueous saturated sodium chloride solution (50 g). The EtOAc extract was dried over anhydrous MgSO4 (10 g). The EtOAc solution was filtered and diluted with DMF (40. g). The ethyl acetate was evaporated at 40° C. under reduced pressure to give the solution of the product in DMF. Weight of solution ˜52 g.

Workup

  1. customThe acetone was removed on a rotary evaporator at 40° C
  2. extractionThe remaining mixture was extracted with ethyl acetate (2×65 mL)
  3. extractionThe EtOAc extract
  4. washwas washed with water (50 g)
  5. extractionThe EtOAc extract
  6. dry with materialwas dried over anhydrous MgSO4 (10 g)
  7. filtrationThe EtOAc solution was filtered
  8. additiondiluted with DMF (40. g)
  9. customThe ethyl acetate was evaporated at 40° C. under reduced pressure
  10. customto give the solution of the product in DMF

Sources & evidence

ORD record
ord-fff245936c25442bbc091f0c38c377aa
Source dataset
uspto-grants-2012_07
Patent number
US08217142B2

Reaction notes

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