4-Nitrophenyl chloroformate → HCID 22625966, compound

HRID 277764Notes

Reaction equation

HRID 277764 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[C:11](=[O:28])[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].C([N-]C(C)C)(C)C.[Li+].Cl[C:38]([O:40][C:41]1[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=1)=[O:39]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[C:11](=[O:28])[N:10]2[C:38]([O:40][C:41]2[CH:42]=[CH:43][C:44]([N+:47]([O-:49])=[O:48])=[CH:45][CH:46]=2)=[O:39])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 821294-Nitrophenyl chloroformateHCID 2724682Lithium diisopropylamideHCID 22625979HCID 22625979, compound

Product 1

HCID 22625966HCID 22625966, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound was prepared by treating 10 (0.292 g, 0.767 mmol) with lithium diisopropylamide (2.0 M THF solution, 1.1 equivalents) in THF at −78° C. for 20 minutes followed by the rapid addition of 4-nitrophenyl chloroformate (1.5 equivalents) in THF. The 1H NMR was consistent with the assigned structure.

Sources & evidence

ORD record
ord-e8ac49f494734f139286e12fbe1b54b8
Source dataset
uspto-grants-2002_03
Patent number
US06358959B1

Reaction notes

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