Acetic Anhydride → (R)-(-)-N-(4-Cyano-2-ethyl-phenyl)-N-[3,4-dioxo-2-(1,2,2-trimethyl-propylamino)-cyclobut-1-enyl]-acetamide

HRID 260801Notes

Reaction equation

HRID 260801 reaction equation
[O:1]=[C:2]1[C:5](=[O:6])[C:4]([NH:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[CH2:16][CH3:17])=[C:3]1[NH:18][C@H:19]([CH3:24])[C:20]([CH3:23])([CH3:22])[CH3:21].[C:25](OC(=O)C)(=[O:27])[CH3:26]>N1C=CC=CC=1>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([N:7]([C:4]2[C:5](=[O:6])[C:2](=[O:1])[C:3]=2[NH:18][C@H:19]([CH3:24])[C:20]([CH3:22])([CH3:21])[CH3:23])[C:25](=[O:27])[CH3:26])=[C:9]([CH2:16][CH3:17])[CH:10]=1)#[N:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 9883778(+)-(R)-4-[3,4-dioxo-2-(1,2,2-trimethyl-propylamino)-cyclobut-1-enylamino]-3-ethylbenzonitrile

Product 1

HCID 54514347(R)-(-)-N-(4-Cyano-2-ethyl-phenyl)-N-[3,4-dioxo-2-(1,2,2-trimethyl-propylamino)-cyclobut-1-enyl]-acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(+)-(R)-4-[3,4-Dioxo-2-(1,2,2-trimethyl-propylamino)-cyclobut-1-enylamino]-3-ethylbenzonitrile (0.36 g, 1.11 mmol), acetic anhydride (0.31 mL, 3.29 mmol) and pyridine (3.4 mL) were mixed and allowed to stand at room temperature for 24 hours. The reaction mixture was filtered to remove undissolved solid material and the filtercake was rinsed with ethyl acetate. The combined filtrate was concentrated and the resulting solid was purified by recrystallization (EtOAc/CH2Cl2) and trituration (EtOAc) to afford the title compound as 0.29 g (71%) of a white solid: mp 229°-231° C.; [α]D25 -224.43° (DMSO, c 0.0092); 1H NMR (CDCl3): δ 7.72 (s, 1H), 7.64 (m, 1H), 7.54-7.40 (m, 1H), 7.38 (m, 1H), 4.37 (m, 1H), 2.72-2.53 (m, 2H), 1.92 (s, 3H), 1.32-1.23 (m, 6H), 0.99 (d, 9H). IR (KBr): 3450, 3340, 2970, 2240, 1800, 1725, 1680, 1610 cm-1 ; MS (m/z) 367 (M+).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove undissolved solid material
  3. washthe filtercake was rinsed with ethyl acetate
  4. concentrationThe combined filtrate was concentrated
  5. customthe resulting solid was purified by recrystallization (EtOAc/CH2Cl2) and trituration (EtOAc)

Sources & evidence

ORD record
ord-9ee20bcaf3e44446a59c5fdf0fba8c42
Source dataset
uspto-grants-1996_06
Patent number
US05530025

Reaction notes

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