Sodium Hydroxide → (2S)-2-Amino-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid

HRID 358561Notes

Reaction equation

HRID 358561 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][NH2:5].Cl.Cl.[OH-].[Na+].[C:13](=[O:16])(O)[OH:14].[CH:17]1[C:29]2[CH:28]([CH:30]3CC(=O)NC3=O)[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]=2[CH:20]=[CH:19][CH:18]=1>O>[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][NH:5][C:13]([O:14][CH2:30][CH:28]1[C:29]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22]2[C:27]1=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2724265(2S)-2,4-Diaminobutanoic acid dihydrochlorideHCID 67856409HCID 67856409, compound

Product 1

HCID 15601076(2S)-2-Amino-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Cupric sulphate (1.4 g, 5.5 mM) in (5.5 cm3) water was added to a stirred solution of H-Dab-OH.2HCl (2 g, 0.5 mM) and NaOH (0.8 g. 0.02 mM) in water (44 cm3), and the resulting mixture stirred for one hour. 9-Fluorenyl succinimide carbonate (3.2 g) was then added dropwise with vigorous stirring and the resulting mixture stirred at room temperature for three days. The precipitate resulting was filtered, washed with water and dried. Excess ethylene diamine tetraacetic acid disodium salt was then added to one liter of boiling water, and the suspension kept at boiling point for ten minutes. The product was filtered, washed with water and dried in high vacuo over phosphorus pentoxide, (3.4 g. 94%), m.p., 166° C.

Workup

  1. stirringwith vigorous stirring
  2. stirringthe resulting mixture stirred at room temperature for three days
  3. customThe precipitate resulting
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried
  7. additionExcess ethylene diamine tetraacetic acid disodium salt was then added to one liter of boiling water
  8. customfor ten minutes
  9. filtrationThe product was filtered
  10. washwashed with water
  11. dry with materialdried in high vacuo over phosphorus pentoxide, (3.4 g. 94%), m.p.
  12. custom166° C.

Sources & evidence

ORD record
ord-4860a2cab9be493a83381232779e18d8
Source dataset
uspto-grants-1991_03
Patent number
US04997648

Reaction notes

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