Water → HCID 18605769, compound

HRID 1249293Notes

Reaction equation

HRID 1249293 reaction equation
[N+](C1C=CC(C[O:9][C:10](=[O:27])[C@H:11]([CH2:23][CH:24]([CH3:26])[CH3:25])[N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:13]2[CH2:15][CH2:14]2)=CC=1)([O-])=O.[OH-].[Na+].O>CO>[C:16]([N:12]([CH:13]1[CH2:15][CH2:14]1)[C@H:11]([C:10]([OH:27])=[O:9])[CH2:23][CH:24]([CH3:26])[CH3:25])([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70473904HCID 70473904, compound

Product 1

HCID 18605769HCID 18605769, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of Boc-cyclopropyl leucine p-nitrobenzyl ester (8) (300 mg, 7.9 mmol) in MeOH (20 ml) was added 2N NaOH soln. (7 ml) under ice cooling and the mixture was stirred for 3 hr at room temperature, the starting material gradually dissolved and the mixture turned yellow. Water (10 ml) was added and the MeOH was evaporated in vacuo. The aqueous residue was washed with AcOEt, cooled in an ice bath and acidified by the addition of 10% citric acid to pH 3. The resulting white precipitate was extracted with AcOEt (3×20 ml) and the extract was washed with sat. NaCl soln, dried over Na2SO4, and evaporated in vacuo. The resulting of Boc-cyclopropyl-leucine (9) was recrystallized from AcOEt-n-hexane to give 140 mg, (72.5%) as colorless prisms; mp 196°-197° C. (dec.); IR: (KBr) 3230(NH), 1690(C=O), 1645(C=O). NMR (CDCl3 +DMSOd6) δ:5.78 (s, 1H, NH), 1.2-1.8 (m,4H,CH2, CHx2),1.4 (s,9H,Boc), 0.9-1.1 (m,6H,(CH3)2CH).

Workup

  1. dissolutionthe starting material gradually dissolved
  2. customthe MeOH was evaporated in vacuo
  3. washThe aqueous residue was washed with AcOEt
  4. temperaturecooled in an ice bath
  5. additionacidified by the addition of 10% citric acid to pH 3
  6. extractionThe resulting white precipitate was extracted with AcOEt (3×20 ml)
  7. washthe extract was washed with sat. NaCl soln
  8. dry with materialdried over Na2SO4
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-ae658eaf26814794a7e7d5547c728073
Source dataset
uspto-grants-1986_12
Patent number
US04629784

Reaction notes

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