Hydrazine hydrate (1:1) → (S)-2-Amino-5,5-dimethoxypentanoic acid, methyl ester

HRID 52802Notes

Reaction equation

HRID 52802 reaction equation
C1(=O)[N:5]([C@@H:6]([CH2:11][CH2:12][CH:13]([O:16][CH3:17])[O:14][CH3:15])[C:7]([O:9][CH3:10])=[O:8])C(=O)C2=CC=CC=C12.O.NN>CO>[NH2:5][C@@H:6]([CH2:11][CH2:12][CH:13]([O:16][CH3:17])[O:14][CH3:15])[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10914214(S)-2-Phthalimido-5,5-dimethoxypentanoic acid, methyl ester

Product 1

HCID 642239(S)-2-Amino-5,5-dimethoxypentanoic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-2-Phthalimido-5,5-dimethoxypentanoic acid, methyl ester [prepared as described in Example 4(f), 3.35 g., 10.43 mmol.) in methanol (70 ml.) was treated with hydrazine monohydrate (531 μl., 10.95 mmol., 1.05 eq.) and the solution was stirred at room temperature for 6 days. The mixture was filtered and the solid was washed with methanol. The filtrate was concentrated, triturated with methylene chloride, filtered again, concentrated, and dried in vacuo to yield 1.89 g. of title product as a cloudy oil. TLC (10% methanol in methylene chloride) Rf =0.39.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with methanol
  3. concentrationThe filtrate was concentrated
  4. customtriturated with methylene chloride
  5. filtrationfiltered again
  6. concentrationconcentrated
  7. customdried in vacuo
  8. customto yield 1.89 g

Sources & evidence

ORD record
ord-14c6e5346757410bb7f289547b120f39
Source dataset
uspto-grants-1997_04
Patent number
US05616775

Reaction notes

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