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Toluene → (2,2-Difluoro-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone trifluoroacetate

HRID 1689283
Notes
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Reaction equation

HRID 1689283 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]1([F:35])[CH2:14][N:13]([C:15]([C:17]2[S:18][C:19]([CH3:22])=[CH:20][CH:21]=2)=[O:16])[CH2:12][C:11]2([CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]2)[O:10]1.C1(C)C=CC=CC=1>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:35][C:9]1([F:8])[CH2:14][N:13]([C:15]([C:17]2[S:18][C:19]([CH3:22])=[CH:20][CH:21]=2)=[O:16])[CH2:12][C:11]2([CH2:23][CH2:24][NH:25][CH2:26][CH2:27]2)[O:10]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57989071Tert-butyl 2,2-difluoro-4-(5-methylthiophene-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 67291912(2,2-Difluoro-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

Trifluoroacetic acid (5 mL) was added to a solution of tert-butyl 2,2-difluoro-4-(5-methylthiophene-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (example 37, step d) (0.4 g) in dichloromethane (20 mL) at 20° C. The solution was allowed to stand at 20° C. for 25 minutes. Toluene (40 mL) was added and the solvents were removed under reduced pressure. The residue was evaporated down twice with acetonitrile. The resultant gum was triturated with ether to afford the subtitled compound. Yield 0.39 g.

Workup

  1. customthe solvents were removed under reduced pressure
  2. customThe residue was evaporated down twice with acetonitrile
  3. customThe resultant gum was triturated with ether

Sources & evidence

ORD record
ord-b968262be0f14375a7beb4e67562ef06
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08148373B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes