Ethanol → HCID 59291551, compound

HRID 383934Notes

Reaction equation

HRID 383934 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][CH2:26]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH2:25][CH3:26])[C:9]1[S:10][C:11]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:13]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 59291403HCID 59291403, compound

Product 1

HCID 59291551HCID 59291551, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[(tert-butoxycarbonyl)amino]-5-phenyl-1,3-thiazole-4-carboxylate in THF were added EtOH, PPh3, and DEAD, followed by stirring at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane: EtOAc) to obtain ethyl 2-[(tert-butoxycarbonyl) (ethyl)amino]-5-phenyl-1,3-thiazole-4-carboxylate as a yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane: EtOAc)

Sources & evidence

ORD record
ord-03dd0956943b46c9b3fd57b60442667d
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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