Water → HCID 54257403, compound

HRID 1017551Notes

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

Participants

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

customthe layers separated
extractionthe aqueous layer was further extracted with DCM
customdried
filtrationfiltered
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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