Ethanolamine → HCID 71243541, compound

HRID 1774459Notes

Reaction equation

HRID 1774459 reaction equation
[NH2:1][C@H:2]([C:7]([O:9][C@H:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][C@:11]1([CH2:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=1)[C:19]1[CH2:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].CCN(CC)CC.[NH2:45][CH2:46][CH2:47][OH:48].C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(Cl)Cl>[NH2:1][C@H:2]([C:7]([O:9][C@H:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][C@:11]1([CH2:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](=[O:34])[NH:45][CH2:46][CH2:47][OH:48])=[CH:31][CH:30]=1)[C:19]1[CH2:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:8])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 71243448HCID 71243448, compound

Product 1

HCID 71243541HCID 71243541, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{[(1′R,2′R)-1′-(L-leucyloxy)-1′,3′-dihydro-1H,2′H-2,2′-biinden-2′-yl]methyl}benzoic acid (24, 130 mg, 0.26 mmol), Et3N (78 mg, 0.78 mmol) and 2-amino ethanol (24 mg, 0.39 mmol) in DCM (5 mL), was added T3P (0.33 mL, 50 wt % solution in ethyl acetate, 0.52 mmol) and then stirred at room temperature for 12 h. The reaction mixture was quenched with water (25 mL) and extracted with DCM (3×25 mL). The separated organic layer was washed with brine (25 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by CombiFlash using 10% methanol in chloroform as an eluent to yield 70 mg (54%) of the title compound as an off white solid.

Workup

  1. customThe reaction mixture was quenched with water (25 mL)
  2. extractionextracted with DCM (3×25 mL)
  3. washThe separated organic layer was washed with brine (25 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by CombiFlash

Sources & evidence

ORD record
ord-d23c4da8f44849e496edf40b1ff610b1
Source dataset
uspto-grants-2016_02
Patent number
US09260376B2

Reaction notes

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