Ethanol → HCID 57936299, compound

HRID 1434971Notes

Reaction equation

HRID 1434971 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:7][CH:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]4[CH:20]=[C:21]([OH:24])[CH:22]=[CH:23][C:17]=4[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH2:5][C:4]([CH3:26])([CH3:25])[NH:3]1.[C:28]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:29]=1.CCO.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:28]([O:24][C:21]1[CH:22]=[CH:23][C:17]2[CH:16]=[C:15]([C:13]3[CH:12]=[CH:11][N:10]=[C:9]([NH:8][CH:6]4[CH2:7][C:2]([CH3:27])([CH3:1])[NH:3][C:4]([CH3:26])([CH3:25])[CH2:5]4)[N:14]=3)[S:19][C:18]=2[CH:20]=1)[CH3:29]

Participants

6

Reactant 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 136119650HCID 136119650, compound

Product 1

HCID 57936299HCID 57936299, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound of Example 153 (76 mg, 0.2 mmol), triphenylphosphine (80 mg, 0.3 mmol) and EtOH (30 mg, 0.65 mmol) were suspended in 8 ml of THF, then diethylazodicarboxylate (52 mg, 0.3 mmol) dissolved in 4 ml THF was added dropwise. This mixture was stirred at room temperature over night and afterwards evaporated. The crude was purified by chromatography on silicagel (DCM/MeOH/ammonia:9/1/0.1). Yield: 33 mg (40%).

Workup

  1. additionwas added dropwise
  2. customafterwards evaporated
  3. customThe crude was purified by chromatography on silicagel (DCM/MeOH/ammonia:9/1/0.1)

Sources & evidence

ORD record
ord-40ede977631d41d5a34b790a46c4a079
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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