Triphenylphosphine → HCID 86661748, compound

HRID 879973Notes

Reaction equation

HRID 879973 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:15][NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH2:13]O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[NH:52]=[N+:53]=[N-:54].CCOC(/N=N/C(OCC)=O)=O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:15][NH:16][S:17]([C:20]1[CH:21]=[CH:22][C:23]([O:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:24][CH:25]=1)(=[O:19])=[O:18])[CH2:13][N:52]=[N+:53]=[N-:54])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 24530Hydrazoic acidHCID 5462977Diethyl azodicarboxylateHCID 66727702HCID 66727702, compound

Product 1

HCID 86661748HCID 86661748, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (S)-2-(benzyloxycarbonylamino)-3-(4-phenoxybenzene sulfonamido) propanol (0.45 g, 1.0 mmol) in toluene (10 mL) was added PPh3 (0.28 g, 1.1 mmol) and the mixture was stirred at RT for 5 min. After adding hydrazoic acid (1.25 M in toluene, 1.04 mL, 1.3 mmol), DEAD (0.17 mL, 1.1 mmol) was added dropwise. The reaction mixture was stirred at RT for 30 min, filtered and solvent was evaporated. The crude residue was chromatographed (silica gel, 30% EtOAc in n-hexane) to afford (R)-2-(benzyloxycarbonylamino)-3-(4-phenoxybenzenesulfon amido) propyl azide as white solid in 60% (0.29 g) yield.

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred at RT for 30 min
  3. filtrationfiltered
  4. customsolvent was evaporated
  5. customThe crude residue was chromatographed (silica gel, 30% EtOAc in n-hexane)

Sources & evidence

ORD record
ord-4331b7d309ac4803b1f7197cc9516b7f
Source dataset
uspto-grants-2015_03
Patent number
US08993544B2

Reaction notes

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