Water → HCID 24820744, compound

HRID 1249291Notes

Reaction equation

HRID 1249291 reaction equation
[N+](C1C=CC(C[O:9][C:10](=[O:24])[C@H:11]([CH3:23])[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:24])=[O:9])[CH3:23])([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 18605768HCID 18605768, compound

Product 1

HCID 24820744HCID 24820744, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Boc-cyclopropylalanine p-nitrobenzyl Ester (4) (450 mg, 1.34 mmol) in MeOH (20 ml) was added 1N NaOH (2.6 ml, 2.6 mmol) at room temperature. After the mixture was stirred for 3 hr, water (10 ml) was added and the MeOH was removed in vacuo. The aqueous residue was washed with Et2O to remove p-nitrobenzyl alcohol and the aqueous layer was separated, cooled in an ice bath and 10% citric acid solution was added to pH 3. The mixture was saturated with NaCl and extracted with AcOEt and the extracts were washed with sat. NaCl solution, dried over Na2SO4 and evaporated in vacuo to give a white solid which was recrystallized from AcOEt-n-hexane to afford 260 mg of Boc-cyclopropyl Alanine (5) (96.3%) as colorless needles, mp 176°-177° C. (dec.); IR (KBr): 3230(NH), 1630-1680 (C=0). NMR (CDCl3 +DMSO)δ: 9.45 (br, s, IH, COOH), 5.88 (br, s, 1H, NH) 1.3-1.7 (m, 2H, CH2), 1.0-1.2 (m, 2H, CH2), 1.50 (s, 9H, Boc).

Workup

  1. customthe MeOH was removed in vacuo
  2. washThe aqueous residue was washed with Et2O
  3. customto remove p-nitrobenzyl alcohol
  4. customthe aqueous layer was separated
  5. temperaturecooled in an ice bath
  6. addition10% citric acid solution was added to pH 3
  7. extractionextracted with AcOEt
  8. washthe extracts were washed with sat. NaCl solution
  9. dry with materialdried over Na2SO4
  10. customevaporated in vacuo
  11. customto give a white solid which
  12. customwas recrystallized from AcOEt-n-hexane

Sources & evidence

ORD record
ord-a2d80612cb2d4b79a625bc552d02e570
Source dataset
uspto-grants-1986_12
Patent number
US04629784

Reaction notes

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