Hydrazine → Tert-butyl 4-(hydrazinecarbonyl)phenethylcarbamate

HRID 44232Notes

Reaction equation

HRID 44232 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:32][NH2:33]>ClCCl.[OH-].[Na+]>[NH:32]([C:15]([C:14]1[CH:18]=[CH:19][C:11]([CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:12][CH:13]=1)=[O:16])[NH2:33]

Participants

6

Reactant 3

HCID 9321HydrazineHCID 682631,1'-CarbonyldiimidazoleHCID 166409054-(2-{[(Tert-butoxy)carbonyl]amino}ethyl)benzoic acid

Product 1

HCID 67434557Tert-butyl 4-(hydrazinecarbonyl)phenethylcarbamate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 4-(2-((tert-butoxycarbonyl)amino)ethyl)benzoic acid (3.364 g, 12.7 mmol) in anhydrous dichloromethane (60 mL) was added carbonyldiimidazole (2.264 g, 13.97 mmol). The reaction mixture was stirred at room temperature for 45 minutes before anhydrous hydrazine (1 ml) was added and the mixture stirred at room temperature for another 16 hours. Evaporation to dryness gave a white solid that was stirred in 1.5N sodium hydroxide (200 mL) for 30 minutes before being filtered off and washed with water (2×100 mL). Drying under vacuum gave tert-butyl 4-(hydrazinecarbonyl)phenethylcarbamate as a white powder (2.847 g). 400 MHz 1H NMR (DMSO-d6) δ: 9.69 (s, 1H), 7.74 (d, J=8 Hz, 2H), 7.25 (d, J=8 Hz, 2H), 6.9 (t, J=5.2 Hz, 1H), 4.45 (s, 2H), 3.15 (m, 2H), 2.72 (t, J=7.6 Hz, 2H), 1.36 (s, 9H). LCMS [M+]: 279.

Workup

  1. additionwas added
  2. customEvaporation to dryness
  3. customgave a white solid
  4. filtrationbefore being filtered off
  5. washwashed with water (2×100 mL)
  6. customDrying under vacuum

Sources & evidence

ORD record
ord-b06cd394aa064a62896f42b51d885a9f
Source dataset
uspto-grants-2013_09
Patent number
US08541407B2

Reaction notes

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