Phosphoric Acid → HCID 10694896, compound

HRID 1597466Notes

Reaction equation

C1(NC2CCCCC2)CCCCC1.[C:14]([C:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=1[NH:28][C@@H:29]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:36][CH:35]=1)[C:30]([OH:32])=[O:31])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O1CCOCC1.O.[OH-].[Li+].P(=O)(O)(O)O>O>[C:14]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][CH:29]([CH2:33][C:34]1[CH:35]=[CH:36][C:37]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:38][CH:39]=1)[C:30]([OH:32])=[O:31])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 185 mg (0.62 mmol) of Intermediate 2 in 8 mL (1:1; dioxane:water) was added 500 mg (11.9 mmol) lithium hydroxide monohydrate. The resulting suspension was stirred at 50° C. for 5 h and then cooled to RT. A 1M phosphoric acid solution was added until pH was 5.5 was reached where upon the resulting suspension was extracted with EtOAc (2×25 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated and chromatographed on silica gel using CH2Cl2/MeOH (9:1) to yield 133 mg of the title compound. 1H NMR (CDCl3) δ 8.87 (bs, 1H) 7.60-7.58 (d, 2H, J=6) 7.94-7.32 m (10H), 7.23-7.21 (d, 2H, J=3.9), 6.90-6.88 (m, 2H) 6.67-6.56 (m, 2H), 4.98 (s, 2H), 4.39 (m, 1H), 3.30-3.10 (m, 2H); low resolution MS (FAB+) m/e (MH+) 452.1.

Workup

temperaturecooled to RT
extractionwas extracted with EtOAc (2×25 mL)
dry with materialThe combined organic extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customchromatographed on silica gel

Sources & evidence

ORD record: ord-42ff740127864d7e89475d3972570516
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06294580B1

Reaction notes

Loading…