4-Nitrophenyl trifluoroacetate → HCID 131711393, compound

HRID 1448869Notes

Reaction equation

HRID 1448869 reaction equation
[NH:1]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C@H:2]([C:6]([N:8]1[CH2:37][CH2:36][CH2:35][C@H:9]1[C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:28]([NH:30][CH2:31][C:32]([OH:34])=[O:33])=[O:29])[CH2:18][CH:19]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:20](=[O:22])[OH:21])=[O:15])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].FC(F)(F)C(O[C:50]1[CH:55]=[CH:54][C:53]([N+:56]([O-:58])=[O:57])=[CH:52][CH:51]=1)=O>N1C=CC=CC=1>[NH:1]([C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39])[C@H:2]([C:6]([N:8]1[CH2:37][CH2:36][CH2:35][C@H:9]1[C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:28]([NH:30][CH2:31][C:32]([O:34][C:50]1[CH:55]=[CH:54][C:53]([N+:56]([O-:58])=[O:57])=[CH:52][CH:51]=1)=[O:33])=[O:29])[CH2:18][CH:19]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:20](=[O:21])[OH:22])=[O:15])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 695694-Nitrophenyl trifluoroacetateHCID 131711392HCID 131711392, compound

Product 1

HCID 131711393HCID 131711393, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

XIX (1.32 g, 2.15 mmol) and p-nitrophenyl trifluoroacetate (0.607 g, 2.58 mmol) were reacted in pyridine (10 ml) in the same manner as described for the preparation of X in part (b). The resulting oil was triturated with ether and petroleum ether. The solid obtained was composed of one major component (Rf1 0.44) and one minor component (Rf1 0.33). Repeated recrystallization from chloroform-petroleum ether and further purifications using several organic solvents were attempted, but these attempts were only of limited effect in fractionating the major component as pure XX. The component (1.13 g, Rf1 0.44) containing only traces of the component (Rf1 0.33) was used in the next step without further purification.

Workup

  1. customThe resulting oil was triturated with ether and petroleum ether
  2. customThe solid obtained
  3. customrecrystallization from chloroform-petroleum ether and further purifications
  4. additionThe component (1.13 g, Rf1 0.44) containing only traces of the component (Rf1 0.33)
  5. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-9637234d16a140a5940763309a82927d
Source dataset
uspto-grants-1980_02
Patent number
US04187852

Reaction notes

Loading…