Triethylamine → HCID 13799233, compound

HRID 1905849Notes

Reaction equation

HRID 1905849 reaction equation
[CH:1]([O:3][C@@H:4]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@H:6]([CH2:7][C:8](=[O:33])[C@@H:9]3[C@@H:24]2[CH2:23][C@H:22]([O:29][CH:30]=[O:31])[C@@:21]2([CH3:32])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:20])[CH2:15][CH2:16][C:17](O)=[O:18])[CH2:5]1)=[O:2].C(N(CC)CC)C.[NH2:41][C:42]([CH3:46])([CH3:45])[CH2:43][OH:44].C(OC(N1C2C(=CC=CC=2)C=CC1OCC)=O)C>C(OCC)(=O)C>[CH:1]([O:3][C@@H:4]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@H:6]([CH2:7][C:8](=[O:33])[C@@H:9]3[C@@H:24]2[CH2:23][C@H:22]([O:29][CH:30]=[O:31])[C@@:21]2([CH3:32])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:20])[CH2:15][CH2:16][C:17]([NH:41][C:42]([CH3:46])([CH3:45])[CH2:43][OH:44])=[O:18])[CH2:5]1)=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 13799231HCID 13799231, compound

Product 1

HCID 13799233HCID 13799233, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of 3α,12α-diformyloxy-7-oxo-5β-cholan-24-oic acid (19 g) in 400 ml of ethyl acetate were added 8.0 ml of triethylamine, a solution of 6.0 ml of 2-amino-2-methyl-1-propanol in 50 ml of ethyl acetate, and 15 g of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline and the mixture was refluxed for 5 hrs. After cooling to room temperature, the reaction mixture was washed successively with water (50 ml×1), 1N HCl solution (50 ml×4), water (50 ml×1), 5% NaHCO3 solution (50 ml×2), and then water to neutrality (50 ml×3). The organic layer was dried over anhydrous Na2SO4, filtered, and evaporated in vacuo to give an oily residue (21.5 g) which could not be crystallized. PMR (δ ppm): 0.66 (3H, s, 18--CH3), 0.85 (3H, d, J=6 Hz, 21--CH3), 1.08 (3H, s, 19--CH3), 1.53 (6H, s, --C(CH3)2 --), 3.88 (2H, s, --CH2OH), 4.71 (1H, m, 3β--H), 5.22 (1H, m, 12β--H), 7.58 (1H, s, --NH--), 8.03 and 8.18 (2H, s, 2×--COH).

Workup

  1. washthe reaction mixture was washed successively with water (50 ml×1), 1N HCl solution (50 ml×4), water (50 ml×1), 5% NaHCO3 solution (50 ml×2)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-9f9157cb4a254568b578887f1971bd1b
Source dataset
uspto-grants-1987_03
Patent number
US04648995

Reaction notes

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