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Dimethylformamide → Tert-butyl 4-(5-bromo-1,3-thiazol-2-yl)-4-hydroxycyclohexanecarboxylate

HRID 1039932
Notes
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Reaction equation

HRID 1039932 reaction equation
[OH:1][C:2]1([C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[CH2:7][CH2:6][CH:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.CN(C=O)C.C1C(=O)N([Br:32])C(=O)C1>O.C(OCC)(=O)C>[Br:32][C:17]1[S:16][C:15]([C:2]2([OH:1])[CH2:7][CH2:6][CH:5]([C:8]([O:10][C:11]([CH3:14])([CH3:12])[CH3:13])=[O:9])[CH2:4][CH2:3]2)=[N:19][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 67257275Tert-butyl 4-hydroxy-4-(1,3-thiazol-2-yl)cyclohexanecarboxylate

Product 1

HCID 70926225Tert-butyl 4-(5-bromo-1,3-thiazol-2-yl)-4-hydroxycyclohexanecarboxylateYield 79.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

To a flask containing the product of Step 1 (925 g, 33 mmol) was added DMF (36 mL) and then n-bromosuccinimide (6.97 g, 32 mmol). The reaction was allowed to stir until complete by LCMS. The reaction was diluted with water and ethyl acetate. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated. Flash chromatography was used for purification to yield tert-butyl 4-(5-bromo-1,3-thiazol-2-yl)-4-hydroxycyclohexane-carboxylate (9.24 g, 25.5 mmol, 78% yield). MS ESI: [M+H]+ m/z 364.0.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customFlash chromatography was used for purification

Sources & evidence

ORD record
ord-74185fe498664d66b3ef942ed999efba
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08551984B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes