Triphenylphosphine → HCID 86666273, compound

HRID 1026244Notes

Reaction equation

HRID 1026244 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:15][CH2:16][C@@H:17]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:46]1([CH2:49][O:50][C:51]2[CH:66]=[CH:65][C:54]3[CH2:55][CH:56]([C:58]4[N:63]=[CH:62][C:61](O)=[CH:60][CH:59]=4)[O:57][C:53]=3[CH:52]=2)[CH2:48][CH2:47]1>C1COCC1.C1(C)C=CC=CC=1>[CH:46]1([CH2:49][O:50][C:51]2[CH:66]=[CH:65][C:54]3[CH2:55][CH:56]([C:58]4[N:63]=[CH:62][C:61]([O:15][CH2:16][C@@H:17]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:18])=[CH:60][CH:59]=4)[O:57][C:53]=3[CH:52]=2)[CH2:47][CH2:48]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamateHCID 67778666HCID 67778666, compound

Product 1

HCID 86666273HCID 86666273, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A toluene solution (1.9 M, 0.474 mL) of diisopropyl azodicarboxylate was added dropwise to a solution of tert-butyl [(1S)-2-hydroxy-1-methylethyl]carbamate (158 mg), triphenylphosphine (236 mg) and 6-[6-(cyclopropylmethoxy)-2,3-dihydro-1-benzofuran-2-yl]pyridin-3-ol (170 mg) in THF (30 mL) at room temperature. The reaction mixture was stirred at room temperature for 16 hr, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (80 mg).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-af87105652534d23b80d78e6aabf9b63
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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