Triphenylphosphine → HCID 58748348, compound

HRID 1875357Notes

Reaction equation

HRID 1875357 reaction equation
[N:1]([CH2:4][C@@H:5]1[CH2:9][C@@H:8]([NH:10][C:11]([C:13]2[S:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[O:12])[CH2:7][N:6]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[NH2:1][CH2:4][C@@H:5]1[CH2:9][C@@H:8]([NH:10][C:11]([C:13]2[S:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[O:12])[CH2:7][N:6]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86761676HCID 86761676, compound

Product 1

HCID 58748348HCID 58748348, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

290.0 mg (0.75 mmol) tert. Butyl (2S,4R)-2-azidomethyl-4-[(5-chloro-thiophene-2-carbonyl)-amino]-pyrrolidine-1-carboxylate are dissolved in a mixture of 4 ml THF and 0.4 ml of water and combined with 0.3 g (1.1 mmol) triphenylphosphine. The reaction mixture is stirred at RT for 16 hours. Then the mixture is concentrated i. vac., combined with water and dil. Sodium hydroxide solution and extracted three times with DCM. The combined organic phases are dried on sodium sulphate, filtered and evaporated down i. vac. The crude product is purified by flash chromatography on silica gel (eluant DCM/methanol 9:1→1:1).

Workup

  1. concentrationThen the mixture is concentrated i
  2. extractionextracted three times with DCM
  3. customThe combined organic phases are dried on sodium sulphate
  4. filtrationfiltered
  5. customevaporated down i
  6. customThe crude product is purified by flash chromatography on silica gel (eluant DCM/methanol 9:1→1:1)

Sources & evidence

ORD record
ord-25df579da4ec47cb97797c4556654556
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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