Triphenylphosphine → HCID 69310397, compound

HRID 2375291Notes

Reaction equation

HRID 2375291 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:15]([O:19][C:20]([NH:22][CH2:23][CH2:24][OH:25])=[O:21])([CH3:18])([CH3:17])[CH3:16].O=[C:27]1[CH:31]=[N:30][S:29][NH:28]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:15]([O:19][C:20]([NH:22][CH2:23][CH2:24][O:25][C:27]1[CH:31]=[N:30][S:29][N:28]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 43405081,2,5-thiadiazol-3-ol

Product 1

HCID 69310397HCID 69310397, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (1.1 ml, 5.5 mmol) was added dropwise to a solution of 2-(t-butoxycarbonylamino)ethanol (850 μl, 5.5 mmol), 3-oxo-2,3-dihydro-1,2,5-thiadiazole (Method 75; 510 mg, 5 mmol) and triphenylphosphine (1.44 g, 5.5 mmol) in THF (20 ml) and the mixture was stirred at ambient temperature for 18 hours. The solvent was evaporated and the residue purified by flash chromatography on silica gel eluting with iso-hexane: EtOAc (100:0 increasing in polarity to 4:1) to give the title compound (1.17 g, 95%) as a white solid. NMR 1.38 (s, 9H), 3.31 (m, 2H), 4.16 (t, 2H), 6.96 (m, 1H), 8.35 (s, 1H); m/z 246.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by flash chromatography on silica gel eluting with iso-hexane: EtOAc (100:0 increasing in polarity to 4:1)

Sources & evidence

ORD record
ord-733f3ba711ce4321b9d9315962b84058
Source dataset
uspto-grants-2008_12
Patent number
US07465728B2

Reaction notes

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