Hydrazine hydrate (1:1) → (S)-tert-Butyl (1-hydrazinyl-1-oxo-3-phenylpropan-2-yl)carbamate

HRID 339273Notes

Reaction equation

HRID 339273 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[NH2:22][NH2:23]>CO>[NH:22]([C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH2:23]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 9882138Boc-L-phenylalanine methyl ester

Product 1

HCID 6710869(S)-tert-Butyl (1-hydrazinyl-1-oxo-3-phenylpropan-2-yl)carbamateYield 65.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate (Aldrich, 300 mg, 1.07 mmol) in MeOH (5.4 mL) was added hydrazine hydrate (170 μL, 3.44 mmol). The resulting solution was stirred at room temperature overnight and then concentrated in vacuo. The residue was triturated with hexanes (2×) and then from a minimal amount of 2:3 hexanes/MeOH (2×) to give the title compound (195 mg, 65%) as a white solid. 1H NMR (CDCl3) δ 7.41-7.25 (m, 3H), 7.20 (d, J=6.8 Hz, 2H), 4.39-4.21 (m, 1H), 3.07 (d, J=7.0 Hz, 2H), 1.42 (s, 9H); MS (ESI+) m/z 280.3 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated with hexanes (2×)

Sources & evidence

ORD record
ord-8deb19f9a01541dea5cbd3f514200779
Source dataset
uspto-grants-2014_11
Patent number
US08889712B2

Reaction notes

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