Hydrazine hydrate (1:1) → tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-amino-propionate

HRID 2298002Notes

Reaction equation

HRID 2298002 reaction equation
[CH2:1]1[O:44][C:43]2[CH:42]=[CH:41][C:5]([CH2:6][N:7]([S:28]([C:31]3[C:36]([CH3:37])=[CH:35][C:34]([O:38][CH3:39])=[CH:33][C:32]=3[CH3:40])(=[O:30])=[O:29])[C@H:8]([CH2:16][N:17]3C(=O)C4=CC=CC=C4C3=O)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=2[O:2]1.O.NN.C(NN)(=O)C1C(=CC=CC=1)C(NN)=O>C(Cl)Cl.CO>[CH2:1]1[O:44][C:43]2[CH:42]=[CH:41][C:5]([CH2:6][N:7]([S:28]([C:31]3[C:32]([CH3:40])=[CH:33][C:34]([O:38][CH3:39])=[CH:35][C:36]=3[CH3:37])(=[O:30])=[O:29])[C@H:8]([CH2:16][NH2:17])[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 11367556PhthalohydrazideHCID 18337583tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-phthalimido-propionate

Product 1

HCID 69762296tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-amino-propionateYield 98.2%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a stirred solution of tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-phthalimido-propionate (3.9 g, 6.2 mmol) in a mixture of 78% methylene chloride/methanol (47 ml) was added hydrazine hydrate (3.9 ml, 125 mmol) and the mixture was stirred for five hours, at which time a solid precipitate of phthalhydrazide was observed to form. The material was filtered, washing with methylene chloride, to remove the precipitate. The filtrate was then evaporated on the rotovap and taken up in methylene chloride (80 ml) and transferred to a separatory funnel. After partitioning with an equal volume of water, the organic phase was collected and washed with an equal volume of brine. The aqueous phases were back extracted with methylene chloride (2×80 ml). The methylene chloride phases were combined, dried (MgSO4), filtered and condensed to provide tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-amino-propionate as a white semi-solid (3.0 g).

Workup

  1. customto form
  2. filtrationThe material was filtered
  3. washwashing with methylene chloride
  4. customto remove the precipitate
  5. customThe filtrate was then evaporated on the rotovap
  6. customtransferred to a separatory funnel
  7. customAfter partitioning with an equal volume of water
  8. customthe organic phase was collected
  9. washwashed with an equal volume of brine
  10. extractionThe aqueous phases were back extracted with methylene chloride (2×80 ml)
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. customcondensed

Sources & evidence

ORD record
ord-63289bbd420d494081a65cef99e0b3d6
Source dataset
uspto-grants-2002_12
Patent number
US06492394B1

Reaction notes

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