Acetaldehyde → HCID 131728516, compound

HRID 1172551Notes

Reaction equation

[CH:1](=O)[CH3:2].[CH3:4][O:5][C:6]([C:8]1[CH:9]=[C:10]([CH3:28])[C:11]2[O:17][C:16]3[C:18]([Cl:24])=[CH:19][C:20]([CH2:22][NH2:23])=[CH:21][C:15]=3[CH2:14][S:13](=[O:26])(=[O:25])[C:12]=2[CH:27]=1)=[O:7].[C:29](O)([C:31](F)(F)F)=O.[BH3-]C#N.[Na+].C(=O)(O)[O-].[Na+]>CO>[CH3:4][O:5][C:6]([C:8]1[CH:9]=[C:10]([CH3:28])[C:11]2[O:17][C:16]3[C:18]([Cl:24])=[CH:19][C:20]([CH2:22][N:23]([CH2:1][CH3:2])[CH2:29][CH3:31])=[CH:21][C:15]=3[CH2:14][S:13](=[O:25])(=[O:26])[C:12]=2[CH:27]=1)=[O:7]

Participants

Conditions

Temperature: 0 °C

Procedure

Acetaldehyde (0.1 ml, 2.35 mmol) was added to a cooled solution of Example 198k (0.2 g, 0.47 mmol) in dry methanol (15 mL). Subsequently TFA (0.036 ml, 0.47 mmol) was added and the reaction mixture was stirred for 2 h. at 0° C. NaBH3CN (0.075 g, 1.17 mmol) was added and the reaction mixture was stirred for 15 h at room temperature. It was treated with a 10% aqueous sodium bicarbonate solution (1 mL) and the solid that precipitated was filtered, washed with water, dried and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound as a white solid. Yield: 0.150 g, (76.53%); 1H NMR (DMSO-d6): δ 1.05 (t, 6H, 2CH3), 2.55 (q, 4H, 2CH2), 2.70 (s, 3H, CH3), 3.55 (s, 2H, CH2), 4.00 (s, 3H, OCH3), 4.70 (s, 2H, CH2), 7.39 (s, 1H, Ar), 7.50 (s, 1H, Ar), 8.10 (s, 1H, Ar), 8.50 (s, 1H, Ar); MS: m/e (ES+) 438 (M+1).

Workup

stirringthe reaction mixture was stirred for 15 h at room temperature
customthe solid that precipitated
filtrationwas filtered
washwashed with water
customdried
custompurified

Sources & evidence

ORD record: ord-61de54ef7ffb43e084aef1cd24d31485
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834001B2

Reaction notes

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