Hydrazine hydrate (1:1) → (S)-benzyl 2-(aminooxy)-3-(4-(benzyloxy)phenyl)propanoate

HRID 576882Notes

Reaction equation

HRID 576882 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([O:27][N:28]2C(=O)C3C(=CC=CC=3)C2=O)[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>O1CCCC1.CO.C(OCC)(=O)C>[NH2:28][O:27][C@@H:16]([CH2:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][CH:13]=1)[C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86663946(S)-benzyl 3-(4-(benzyloxy)phenyl)-2-(1,3-dioxoisoindolin-2-yloxy)propanoate

Product 1

HCID 86663949(S)-benzyl 2-(aminooxy)-3-(4-(benzyloxy)phenyl)propanoate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixed solution of (S)-benzyl 3-(4-(benzyloxy)phenyl)-2-(1,3-dioxoisoindolin-2-yloxy)propanoate (Compound XXVIII-1) 15.02 g (29.6 mmol) in tetrahydrofuran 60 ml and methanol 60 ml, hydrazine monohydrate 4.31 ml (88.8 mmol) was added and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate 500 ml and washed with saturated sodium bicarbonate solution 200 ml, water 200 ml and brine 200 ml. The organic phase was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound, which was used without further purification.

Workup

  1. washwashed with saturated sodium bicarbonate solution 200 ml, water 200 ml and brine 200 ml
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ac08e53707134bcfa90a194687159ed5
Source dataset
uspto-grants-2015_05
Patent number
US09040531B2

Reaction notes

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