Tributylphosphine → (R)-N-(2,4-Dimethoxybenzyl)-5-fluoro-3-(1-(2-iodophenyl)ethyl)-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

HRID 920259Notes

Reaction equation

HRID 920259 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:4]=1[CH2:5][N:6]([C:21]1[S:25][N:24]=[CH:23][N:22]=1)[S:7]([C:10]1[C:19]([F:20])=[CH:18][C:13]2[NH:14][C:15](=[O:17])[O:16][C:12]=2[CH:11]=1)(=[O:9])=[O:8].C(P(CCCC)CCCC)CCC.CCOC(/N=N/C(OCC)=O)=O.[I:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=1[C@@H:64](O)[CH3:65]>C1COCC1>[CH3:1][O:2][C:3]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:4]=1[CH2:5][N:6]([C:21]1[S:25][N:24]=[CH:23][N:22]=1)[S:7]([C:10]1[C:19]([F:20])=[CH:18][C:13]2[N:14]([C@@H:64]([C:59]3[CH:60]=[CH:61][CH:62]=[CH:63][C:58]=3[I:57])[CH3:65])[C:15](=[O:17])[O:16][C:12]=2[CH:11]=1)(=[O:8])=[O:9]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10514669(1S)-1-(2-iodophenyl)ethanolHCID 89525954N-(2,4-dimethoxybenzyl)-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

Product 1

HCID 117629573(R)-N-(2,4-Dimethoxybenzyl)-5-fluoro-3-(1-(2-iodophenyl)ethyl)-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Added N-(2,4-dimethoxybenzyl)-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide (11-3, 2 g, 4.29 mmol) to THF (21.44 ml). Added tri-n-butylphosphine (2.116 ml, 8.58 mmol) and DEAD (1.358 ml, 8.58 mmol) and cooled to 0° C. Was a clear orange solution. Added (S)-1-(2-iodophenyl)ethanol (16-2, 1.064 g, 4.29 mmol). After 24 h at 0° C., concentrated in vacuo, dissolved in 5 mL DCM and purified by normal-phase HPLC (80 g ISCO column, 0-50% EtOAc:Hex) to give 32-1 as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutiondissolved in 5 mL DCM
  3. custompurified by normal-phase HPLC (80 g ISCO column, 0-50% EtOAc:Hex)

Sources & evidence

ORD record
ord-3614259570ce4e3fb9c32b5a5c558413
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

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