N-(2,4-Dinitrophenyl)glycine → HCID 86609788, compound

HRID 17761Notes

Reaction equation

HRID 17761 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][NH:10][C:11](=[O:42])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][S:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.CN(C)CCCN=C=NCC.[N+:55]([C:58]1[CH:63]=[C:62]([N+:64]([O-:66])=[O:65])[CH:61]=[CH:60][C:59]=1[NH:67][CH2:68][C:69](O)=[O:70])([O-:57])=[O:56]>ClCCl>[N+:55]([C:58]1[CH:63]=[C:62]([N+:64]([O-:66])=[O:65])[CH:61]=[CH:60][C:59]=1[NH:67][CH2:68][C:69]([NH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][NH:10][C:11](=[O:42])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][S:22][C:23]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:70])([O-:57])=[O:56]

Participants

5

Reactant 3

HCID 14135N-(2,4-Dinitrophenyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86609789HCID 86609789, compound

Product 1

HCID 86609788HCID 86609788, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3 (0.25 g, 0.42 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.1 g, 0.5 mmol) in dichloromethane (50 mL) was added N-(2,4-dinitrophenyl)glycine (0.11 g, 0.51 mmol), and the solution was left to react at room temperature overnight. The solution was washed with 0.01 M HCl (1×100 mL), 0.2 M NaOH (1×100 mL), and brine solution (1×100 mL). The solution was dried (MgSO4) and evaporated to dryness. The crude compound was chromatographed (SiO2/EtOAc→MeOH) to yield 0.26 g (0.33 mmol, 79%) of 6 as a yellow oil. 1H NMR (CDCl3, 500 MHz): δ1.12-1.42 (br m, 14H), 1.57-1.62 (br m, 2H), 1.63-1.72 (br t, 2H), 2.12-2.21 (br m, 2H), 3.41-3.61 (br m, 12H), 4.17-4.21 (d, 2H), 5.87-5.92 (br s, 1H), 6.89-6.94 (d, 1H), 7.14-7.24 (m, 6H), 7.31-7.39 (m, 9H), 8.26-8.32 (d, 1H), 9.14-9.21 (br d, 1H). C44H55N5O8S (813.38): m/z 812.7 [M−H+]−.

Workup

  1. waitthe solution was left
  2. customto react at room temperature overnight
  3. washThe solution was washed with 0.01 M HCl (1×100 mL), 0.2 M NaOH (1×100 mL), and brine solution (1×100 mL)
  4. dry with materialThe solution was dried (MgSO4)
  5. customevaporated to dryness
  6. customThe crude compound was chromatographed (SiO2/EtOAc→MeOH)

Sources & evidence

ORD record
ord-7d4f658e063d4675a4603fe6b64c0cb6
Source dataset
uspto-grants-2010_06
Patent number
US07741014B2

Reaction notes

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