Hydrochloric Acid → HCID 91261222, compound

HRID 2428057Notes

Reaction equation

HRID 2428057 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][C@H:14]([CH3:35])[C@H:15]([OH:34])[C@@H:16]([CH3:33])[CH:17]=[CH:18][CH2:19][CH2:20][C@@H:21]([OH:32])[C@@H:22]([CH3:31])[C@H:23]([OH:30])[C@@H:24]([CH3:29])[CH:25]=[CH:26][CH:27]=[CH2:28].O[Li].O.Cl>C1COCC1.O>[OH:34][C@H:15]([C@@H:16]([CH3:33])[CH:17]=[CH:18][CH2:19][CH2:20][C@@H:21]([OH:32])[C@@H:22]([CH3:31])[C@H:23]([OH:30])[C@@H:24]([CH3:29])[CH:25]=[CH:26][CH:27]=[CH2:28])[C@@H:14]([CH3:35])[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:36])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 131725992HCID 131725992, compound

Product 1

HCID 91261222HCID 91261222, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

To an above solution 48 (8.0 mg) in THF-H2O (0.3 ml, 0.1 ml each) was added LiOH·H2O (1.3 mg) and the solution was warmed to 60° C. After stirring 6 h, 1N HCl (1 ml) was added and reaction mixture was extracted with CH2Cl2 (10 ml×2). After drying over MgSO4 and evaporation under vacuum, the crude was chromatographed on SiO2 (EtOAc/hexane 1:3) to yield 6.3 mg (81%) of the 49 as a colorless oil: IR (CHCl3) 3412, 2964, 2921, 2850, 2658, 1710, 1459, 1404, 1268, 971, 903 cm−1; 1H NMR (300 MHz, CDCl3) δ 6.64 (ddd, J=16.7, 10.6, 10.0 Hz, 1H), 6.20 (apparent t, J=10.9 Hz, 1H), 5.54-5.46 (m, 1H), 5.42-5.36 (m, 2H), 5.32-5.18 (m, 4H), 3.88-3.84 (m, 1H), 3.48 (d, J=9.2 Hz, 1H), 3.23 (apparent t, J=5.7 Hz, 1H), 2.86-2.76 (m, 1H), 2.69-2.60 (m, 2H), 2.34 (t, J=7.4 Hz, 2H), 2.21-2.04 (m, 5H), 1.70-1.62 (m, 5H), 1.28 (br, 13H), 1.00 (d, J=6.8 Hz, 3H), 0.98 (d, J=6.9 Hz, 3H), 0.94 (d, J=6.7 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 180.6, 134.4, 133.8, 132.1, 132.0, 132.0, 131.3, 128.8, 119.1, 80.7, 79.2, 76.2, 37.6, 35.5, 34.6, 29.8, 29.7, 29.5, 29.2, 29.1, 29.0, 27.6, 24.8, 24.2, 22.8, 18.1, 16.7, 15.4, 14.2, 4.5; LRMS (API-ES) 515.3 (M+Na)+, 493 (M+H)+, 475 (M+H—H2O)+, 457 (M+H-2H2O)+, 242; [α]20D+33.0 (c 0.23, CHCl3).

Workup

  1. customreaction mixture
  2. extractionwas extracted with CH2Cl2 (10 ml×2)
  3. dry with materialAfter drying over MgSO4 and evaporation under vacuum
  4. customthe crude was chromatographed on SiO2 (EtOAc/hexane 1:3)

Sources & evidence

ORD record
ord-8cd9b543a36e4ba09ba133012be1c952
Source dataset
uspto-grants-2011_06
Patent number
US07968736B2

Reaction notes

Loading…