Dimethyl N-(2-nitrophenyl)-D-aspartate → HCID 11172036, compound

HRID 1868547Notes

Reaction equation

HRID 1868547 reaction equation
C[O:2][C:3](=O)[C@H:4]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-])=O)[CH2:5][C:6]([O:8][CH3:9])=[O:7]>CO.O=[Pt]=O>[CH3:9][O:8][C:6](=[O:7])[CH2:5][C@@H:4]1[C:3](=[O:2])[NH:17][C:12]2[C:11](=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:10]1

Participants

4

Reactant 1

HCID 58648591Dimethyl N-(2-nitrophenyl)-D-aspartate

Product 1

HCID 11172036HCID 11172036, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(R)-(2-nitrophenylamino)succinic acid dimethyl ester (2.15 g, 7.62 mmol) (prepared below), and PtO2 (210 mg) in methanol (35 mL) was shaken on a Parr apparatus at 48 psi for 6 hours. The reaction was filtered through celite, rinsed with methanol and was evaporated in vacuo to a very sticky oil as the title compound (1.69 g, 100%): 1H NMR (CDCl3) δ=8.23 (bs, 1H), 6.91 (dt, 1H, J=1.8, 7.5 Hz), 6.80-6.70 (m, 3H), 4.74 (bs, 1H), 4.34 (dt, 1H, J=2.4, 10.5 Hz), 3.75 (s, 3H), 3.14 (dd, 1H, J=2.4, 17.4 Hz), 2.75 (dd, 1H, J=10.5, 17.4 Hz).

Workup

  1. filtrationThe reaction was filtered through celite
  2. washrinsed with methanol
  3. customwas evaporated in vacuo to a very sticky oil as the title compound (1.69 g, 100%)

Sources & evidence

ORD record
ord-ea642a360f7f4a1f88d20135960e16c7
Source dataset
uspto-grants-2009_12
Patent number
US07635775B2

Reaction notes

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