Tributylphosphine → HCID 131733390, compound

HRID 2274370Notes

Reaction equation

HRID 2274370 reaction equation
[Si:1]([O:8][C@@H:9]1[C@H:14]([OH:15])[C:13]([CH2:16][CH2:17][N:18]([CH3:29])[S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:12][CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O[C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=1[O:39][CH2:40][O:41][CH3:42])[CH:34]=[O:35].P(CCCC)(CCCC)CCCC.CN(C(/N=N/C(N(C)C)=O)=O)C>C1COCC1>[Si:1]([O:8][C@@H:9]1[C@@H:14]([O:15][C:31]2[CH:32]=[C:33]([CH:34]=[O:35])[CH:36]=[CH:37][C:38]=2[O:39][CH2:40][O:41][CH3:42])[C:13]([CH2:16][CH2:17][N:18]([CH3:29])[S:19]([C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)(=[O:20])=[O:21])=[CH:12][CH2:11][CH2:10]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 5353800DiamideHCID 12397048HCID 12397048, compoundHCID 102143846HCID 102143846, compound

Product 1

HCID 131733390HCID 131733390, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of alcohol 14 (190 mg, 0.43 mmol) and phenol 18 (102 mg, 0.56 mmol) in THF (6 mL) at −10° C. was added PBu3 (0.15 mL, 0.65 mmol) followed by tetramethylazodicarboxamide (TMAD) (111 mg, 0.65 mmol). The reaction mixture was slowly warmed to room temperature and was stirred for 22 hours. Solvent was evaporated under reduced pressure and purified by flash column chromatography on silica gel using [hexane/EtOAc (80:20)→hexane/EtOAc (50:50)] as eluent to isolate product 19b (130 mg, 0.22 mmol, 50%) as a clear oil.

Workup

  1. customSolvent was evaporated under reduced pressure
  2. custompurified by flash column chromatography on silica gel using [hexane/EtOAc (80:20)→hexane/EtOAc (50:50)] as eluent

Sources & evidence

ORD record
ord-ec8592ddeb784b9aaa52b5ea30a63205
Source dataset
uspto-grants-2015_09
Patent number
US09126965B1

Reaction notes

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