4-Nitrophenol → Boc-Gly-ONp

HRID 587230Notes

Reaction equation

HRID 587230 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:11]([NH:18][CH2:19][C:20](O)=[O:21])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:14]([O:13][C:11]([NH:18][CH2:19][C:20]([O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:21])=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 77217Boc-Gly-ONp

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-nitrophenol (1.0 g, 7.19 mmol) in CH2Cl2 (20.0 mL) was added N-Boc glycine (1.38 g, 7.91 mmol) and EDC HCl (2.05 g, 10.785 mmol) and the reaction was stirred at ambient temperature for 24 h. The reaction mixture was diluted with CH2Cl2 and washed with water and saturated brine solution. The separated CH2Cl2 layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the title compound as a light brown gummy material that was used in the next step without further purification (1.1 g): 1H NMR (400 MHz, CDCl3) δ 8.29 (d, J=9.2 Hz, 2H), 7.33 (d, J=8.8 Hz, 2H), 5.07 (br, 1H), 4.20 (s, 2H), 1.47 (s, 9H); ESIMS m/z 296.27 ([M+H]+).

Workup

  1. washwashed with water and saturated brine solution
  2. dry with materialThe separated CH2Cl2 layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-11a4217862bd4303ab3eb3932408ea0b
Source dataset
uspto-grants-2016_01
Patent number
US09226500B2

Reaction notes

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