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Water → HCID 54257403, compound

HRID 1017551
Notes
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Reaction equation

HRID 1017551 reaction equation
[CH2:1]([O:8][C:9](=[O:34])[CH2:10][CH:11]([S:19]([N:21]1[CH2:26][CH2:25][CH:24]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][CH2:22]1)=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.CC[O:38]C(C)=O>C(#N)C.C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:34])[CH2:10][CH:11]([S:19]([N:21]1[CH2:26][CH2:25][CH:24]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:23][CH2:22]1)(=[O:38])=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 54183392HCID 54183392, compound

Product 1

HCID 54257403HCID 54257403, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344
Dichloromethane
Solvent

Conditions

Temperature
0 °C

Procedure

The product from Step D (430 mg, 0.91 mmol) was taken up in acetonitrile (1.5 mL) with stirring and cooled to 0° C. RuCl3.3H2O (0.5 mg) and NalO4 (290 mg, 1.37 mmol) were added followed by water (2 mL). The resulting mixture was stirred at room temperature for 2½h until tlc (hex/EtOAc 1:1) indicated the absence of starting material. The reaction was diluted with DCM, the layers separated and the aqueous layer was further extracted with DCM. The organic extracts were combined, dried, filtered and concentrated in vacuo to give the product as an oil (360 mg, 81%). 1H-NMR δ (CDCl3) 7.37-7.09 (15H, m), 4.96 (1H, d, J=12.2 Hz), 4.94 (1H, d, J=12.1 Hz), 3.91 (1H, m), 3.89-3.68 (2H, m), 3.31 (1H, dd, J=4.5, 14.0 Hz), 2.88-2.45 (7H, m 1.72-1.50 (3H, m) and 1.29-1.15 (2H, m).

Workup

  1. customthe layers separated
  2. extractionthe aqueous layer was further extracted with DCM
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d1d49b87ec24aceaef900162946b0c9
Source dataset
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06479502B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes