Formaldehyde → HCID 68115436, compound

HRID 1503901Notes

Reaction equation

[CH2:1]([O:3][CH2:4][CH2:5][CH:6]1[CH2:17][CH2:16][C:15]2[S:14][C:13]3[N:12]=[CH:11][N:10]=[C:9]([O:18][CH:19]4[CH2:24][CH2:23][CH:22]([N:25]([CH3:33])[C:26](=O)OC(C)(C)C)[CH2:21][CH2:20]4)[C:8]=3[C:7]1=2)[CH3:2].C=O>C(O)=O>[CH2:1]([O:3][CH2:4][CH2:5][CH:6]1[CH2:17][CH2:16][C:15]2[S:14][C:13]3[N:12]=[CH:11][N:10]=[C:9]([O:18][CH:19]4[CH2:20][CH2:21][CH:22]([N:25]([CH3:33])[CH3:26])[CH2:23][CH2:24]4)[C:8]=3[C:7]1=2)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A 25-mL round-bottom flask containing 19.1 (19 mg, 0.04 mmol, 1.00 equiv), formic acid (1 mL) and formaldehyde (37%, 5 mL) was heated at 100° C. for 12 h in an oil bath under nitrogen. The mixture was concentrated under reduced pressure and the residue (45 mg) purified by preparative HPLC(SHIMADZU) under the following conditions: column: Xbridge Prep C18, 19*150 mm 5 um; mobile phase: water (0.05% NH4HCO3) and CH3CN (5.0% CH3CN up to 53.0% in 16 min); UV detection at 254 and 220 nm. The product-containing fractions were collected and evaporated under reduced pressure to afford compound I-31 (5.7 mg, 37%) as an off-white oil. 1H NMR (300 MHz, CDCl3) δ 1.20 (m, 3H), 1.54 (m, 4H), 1.61 (m, 1H), 2.02-2.80 (m, 14H), 2.28-3.10 (m, 2H), 3.48 (m, 5H), 5.24 (m, 1H), 8.50 (s, 1H). MS: m/z 390 (M+H)+.

Workup

concentrationThe mixture was concentrated under reduced pressure
customthe residue (45 mg) purified by preparative HPLC(SHIMADZU) under the following conditions
customThe product-containing fractions were collected
customevaporated under reduced pressure
customto afford compound

Sources & evidence

ORD record: ord-8a555f62280541cfb66adfa16d9fbd07
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212190B2

Reaction notes

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