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HCID 86648519, compound → Ethyl 2-[bis(tert-butoxycarbonyl)amino]-4-(1-hydroxypropyl)-1,3-thiazole-5-carboxylate

HRID 1424982
Notes
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Reaction equation

HRID 1424982 reaction equation
[C:1]([O:5][C:6]([N:8]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:9]1[S:10][C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:12]([CH:14]=[O:15])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:28]([Mg]Br)[CH3:29]>C(OCC)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6]([N:8]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[C:9]1[S:10][C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:12]([CH:14]([OH:15])[CH2:28][CH3:29])[N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 86648519HCID 86648519, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 67548974Ethyl 2-[bis(tert-butoxycarbonyl)amino]-4-(1-hydroxypropyl)-1,3-thiazole-5-carboxylateYield 33%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 3283Diethyl Ether
Solvent
2×

Conditions

Temperature
-78 °C

Procedure

Ethyl 2-[bis(tert-butoxycarbonyl)amino]-4-formyl-1,3-thiazole-5-carboxylate obtained in Example (62d) (915.5 mg, 2.29 mmol) was dissolved in diethyl ether (30 mL), followed by cooling to −78° C. Then, tetrabutylammonium bromide (890 mg, 2.76 mmol) and ethylmagnesium bromide (1 M solution in THF, 2.8 mL) were added, and the mixture was stirred for one hour. Diethyl ether was added to the reaction solution, and the organic layer was washed with brine and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=91/9, 85/15) to obtain 327.2 mg of the title compound (33%).

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentration under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=91/9, 85/15)

Sources & evidence

ORD record
ord-51469568ce6f4934873214bfd9a130c4
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08927588B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes