Dimethyl acetylenedicarboxylate → HCID 20605634, compound

HRID 481063Notes

Reaction equation

HRID 481063 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([N:13]([CH2:25]C(O)=O)[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:29]([C:35]([O:37][CH3:38])=[O:36])#[C:30][C:31]([O:33][CH3:34])=[O:32]>C(OC(=O)C)(=O)C>[CH3:34][O:33][C:31]([C:30]1[C:29]([C:35]([O:37][CH3:38])=[O:36])=[CH:25][N:13]([CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)[C:11]=1[CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:32]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 22318856HCID 22318856, compound

Product 1

HCID 20605634HCID 20605634, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of {(3-tert-Butoxycarbonylamino-propionyl)-[2-(4-nitro-phenyl)-ethyl]-amino}-acetic acid (0.253 mmol) in 1 ml acetic anhydride is dimethyl acetylene dicarboxylate (0.278 mmol) added. After stirring at 85° C. for 4½ hours the solvent is evaporated in vacuo. The dark brown oil is chromatographed using ethyl acetate 2:Hexane 3 as a mobile phase to yield 2-(2-tert-Butoxycarbonylamino-ethyl)-1-[2-(4-nitro-phenyl)-ethyl]-1H-pyrrole-3,4-dicarboxylic acid dimethyl ester, 79 mg, as a yellow oil (66%): 1H NMR (CD3OD) 1.50 (s, 9H), 2.84 (t, 2H), 3.14-3.34 (m, 4H), 3.77 (s, 3H), 3.82 (s, 3H), 4.33 (t, 2H), 6.74 (t, 1H), 7.29 (s, 1H), 7.44 (d, 2H), 8.16 (d, 2H) LRMS calcd 475.50, found [M] 475.1.

Workup

  1. additionadded
  2. customis evaporated in vacuo
  3. customThe dark brown oil is chromatographed

Sources & evidence

ORD record
ord-cfd035e244af4fd8aa69b1553587925a
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

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