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Triethylamine → HCID 59331390, compound

HRID 1881908
Notes
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Reaction equation

HRID 1881908 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:17][C@H:18]2[CH2:38][CH2:37][C:20]3([O:24][C@H:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C@@H:22]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[O:21]3)[CH2:19]2)[C:13](=[O:16])[CH:14]=[CH2:15])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[O:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]1[O:45][CH2:46][C:47]1[S:51][C:50]([CH:52]=[O:53])=[N:49][CH:48]=1.C(N(CC)CC)C>C(O)C.[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:17][C@H:18]2[CH2:38][CH2:37][C:20]3([O:21][C@H:22]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@@H:23]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[O:24]3)[CH2:19]2)[C:13](=[O:16])[CH2:14][CH2:15][C:52]([C:50]2[S:51][C:47]([CH2:46][O:45][CH:40]3[CH2:41][CH2:42][CH2:43][CH2:44][O:39]3)=[CH:48][N:49]=2)=[O:53])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 593313055-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazole-2-carbaldehydeHCID 593315944-[3-chloro-4-(methylsulfonyl)phenyl]-5-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]pent-1-en-3-one

Product 1

HCID 59331390HCID 59331390, compoundYield 56.1%

Reagents, catalysts & solvents 3

HCID 2833352
3-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride
Catalyst
HCID 702EthanolSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[3-chloro-4-(methylsulfonyl)phenyl]-5-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]pent-1-en-3-one (525 mg) in ethanol (3 mL) were added 5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazole-2-carbaldehyde (259 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (28.3 mg) and triethylamine (57 μL), and the mixture was stirred with heating under reflux for 1.5 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (416 mg, yield 56%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 1.5 hr
  3. washwashed with water
  4. dry with materialThe ethyl acetate layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-be401f20df57400a954aed6529c0b241
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318746B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes