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Potassium Carbonate → HCID 86653645, compound

HRID 2064810
Notes
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Reaction equation

HRID 2064810 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:23]2[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=2)=[C:5]([C:7]([N:9]2[C@H:14]([CH2:15][NH:16]C(=O)C(F)(F)F)[CH2:13][C@H:12]3[C@@H:10]2[CH2:11]3)=[O:8])[N:6]=1.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+].CC(OC)(C)C>CO.CCOC(C)=O>[NH2:16][CH2:15][C@@H:14]1[CH2:13][C@H:12]2[C@H:10]([CH2:11]2)[N:9]1[C:7]([C:5]1[N:6]=[C:2]([NH2:1])[S:3][C:4]=1[C:23]1[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=1)=[O:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 86653644HCID 86653644, compound

Product 1

HCID 86653645HCID 86653645, compound

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of N-[(1S,3S,5S)-2-(2-amino-5-m-tolyl-thiazole-4-carbonyl)-2-aza-bicyclo[3.1.0]hex-3-ylmethyl]-2,2,2-trifluoro-acetamide (2.33 mmol) in MeOH (7.7 mL) is treated with a sat. aqueous K2CO3 solution (0.62 mL) and stirred at 60° C. for 5 h. After stirring for additional 16 h at RT the mixture is made basic by slow addition of aqueous NaOH solution (32%). Equal volumes of TBME and EtOAc are added and the mixture is stirred vigorously for 1 h. The layers are separated, the aqueous layer is extracted with a mixture of TBME and EtOAc and the combined organic layers are dried over Na2SO4. The solvents are removed in vacuo to give the desired product which is used without further purification. LC-MS (basic): tR=0.67 min; [M+H]+=329.0.

Workup

  1. stirringAfter stirring for additional 16 h at RT the mixture
  2. stirringthe mixture is stirred vigorously for 1 h
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with a mixture of TBME and EtOAc
  5. dry with materialthe combined organic layers are dried over Na2SO4
  6. customThe solvents are removed in vacuo

Sources & evidence

ORD record
ord-eaf2007fce32461e8e073a5dde9fda87
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08288435B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes