Sodium Bicarbonate → HCID 9869745, compound

HRID 1359152Notes

Reaction equation

O[C:2]([C:7]1[CH:20]=[C:19]2[C:10]([C:11]3[C:12]([CH3:36])=[CH:13][C:14]([OH:35])=[CH:15][C:16]=3[CH:17]=[C:18]2[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:23][CH:22]=2)=[CH:9][CH:8]=1)([CH3:6])[CH:3]([CH3:5])[CH3:4].[C:37]([O-])(O)=O.[Na+]>C(O)(=O)C.OS(O)(=O)=O>[CH3:6][C:2]([C:7]1[CH:20]=[C:19]2[C:10]([C:11]3[C:12]([CH3:36])=[CH:13][C:14]([OH:35])=[CH:15][C:16]=3[CH:17]=[C:18]2[C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][N:30]3[CH2:37][CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:25][CH:26]=2)=[CH:9][CH:8]=1)=[C:3]([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 75 °C

Procedure

The compound from Step A (0.587 g, 1.2 mmol) was dissolved in glacial acetic acid (7.0 ml) and concentrated H2SO4 (1 drop) was added. The mixture was heated for 20 min at 75° C. with stirring. The reaction was neutralized with NaHCO3 (10.5 g in 25 ml of water) and extracted with methyl t-butyl ether (3×25 ml), evaporated and dried under high vacuum. The residue was chromatographed on silica gel with acetone/hexane (1:2) to give 0.407 g (85%) of the title compound. 1H-NMR (400 MHz, CDCl3) δH 0.77 (3H, d, CH3), 0.83 (3H, d, CH3), 1.47 (3H, s, CH3), 1.55 (2H, m, NCH2CH2CH2), 1.76 (4H, m, NCH2CH2CH2), 2.72 (4H, br, NCH2CH2CH2), 2.95 (2H, t, OCH2CH2N), 3.11 (3H, s, CH3), 4.24 (2H, t, OCH2CH2N), 6.87-8.78 (10H, ArH).

Workup

extractionextracted with methyl t-butyl ether (3×25 ml)
customevaporated
customdried under high vacuum
customThe residue was chromatographed on silica gel with acetone/hexane (1:2)

Sources & evidence

ORD record: ord-9f594dec6fcd4abe8c1e9d7feeb52bcb
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599921B2

Reaction notes

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