Triphenylphosphine → HCID 67235192, compound

HRID 1521691Notes

Reaction equation

HRID 1521691 reaction equation
O[CH2:2][CH2:3][C:4]([NH:7][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])([CH3:6])[CH3:5].[NH:27]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:38]([O:37][C:35]([N:27]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[CH2:2][CH2:3][C:4]([NH:7][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])([CH3:6])[CH3:5])=[O:36])([CH3:41])([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 279800Di-tert-butyl IminodicarboxylateHCID 67236483HCID 67236483, compound

Product 1

HCID 67235192HCID 67235192, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of benzyl 3-[(4-hydroxy-2-methylbutan-2-yl)amino]-4-nitrobenzoate (395 mg, 1.10 mmol), di-tert-butyl iminodicarboxylate (367 mg, 1.65 mmol), and triphenylphosphine (430 mg, 1.65 mmol) in THF (5 mL) is added diisopropyl azodicarboxylate (0.34 mL, 1.65 mmol). After 16 h at room temperature the solvent is evaporated and the residue is purified by flash chromatography on silica eluting with a heptane/EtOAc gradient to afford the title compound (280 mg, 0.50 mmol, 46%).

Workup

  1. customAfter 16 h at room temperature the solvent is evaporated
  2. customthe residue is purified by flash chromatography on silica eluting with a heptane/EtOAc gradient

Sources & evidence

ORD record
ord-3d1d8a1dca04472088a0f053898ca09b
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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