Triethylamine → N1-((1S,2R)-1-Benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-5-ethyl-N3,N3-dipropylisophthalamide

HRID 14017

Reaction equation

HRID 14017 reaction equation
C(P(=O)([O:7][CH2:8][CH3:9])OCC)#N.NC([C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([C:23]([N:25]([CH2:29][CH2:30][CH3:31])[CH2:26][CH2:27][CH3:28])=[O:24])[CH:22]=1)[C:17](O)=O)=O.FC(F)(F)C(O)=O.[NH2:39][C@@H:40]([CH2:54][C:55]1[CH:60]=[C:59](F)[CH:58]=[C:57](F)[CH:56]=1)[C@H:41]([OH:53])[CH2:42][NH:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([O:51][CH3:52])[CH:46]=1.C(N(CC)CC)C>ClCCl>[CH2:54]([C@H:40]([NH:39][C:8](=[O:7])[C:9]1[CH:17]=[C:16]([CH2:15][CH3:14])[CH:20]=[C:21]([C:23]([N:25]([CH2:29][CH2:30][CH3:31])[CH2:26][CH2:27][CH3:28])=[O:24])[CH:22]=1)[C@H:41]([OH:53])[CH2:42][NH:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([O:51][CH3:52])[CH:46]=1)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 223948913-Carbamoyl-5-dipropylcarbamoyl-benzoic acidHCID 69869154(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol Trifluoroacetate

Product 1

HCID 68609903N1-((1S,2R)-1-Benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-5-ethyl-N3,N3-dipropylisophthalamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22.5 °C

Procedure

Diethyl cyanophosphonate (0.132 mL, 0.870 mmol) is added to a mixture of 3-[(dipropylamino)carbonyl]-5-ethylbenzoic acid (IX, PREPARATION 21, 0.200 g, 0.720 mmol), (2R,3S)-3-amino-1-[(3-methoxybenzyl)amino]-4-phenyl-2-butanol (VIII, EXAMPLE 175, 0.216 mg, 0.720 mmol), and triethylamine (0.121 mL, 0.870 mmol) in dichloromethane (3 mL). The mixture was stirred for 1 hour at 20-25 degrees C. Dichloromethane is then removed under reduced pressure. The residue is partitioned between ethyl acetate and water. The organic phase is separated and is washed with saline, dried over anhydrous sodium sulfate, filtered and concentrated. The concentrate is column chouromatographed (silica gel; methanol/dichloromethane, 5/95) to give the title compound, MS (ESI+) for C34H45N3O4 m/z (M+H)+=560.4; HOURMS (FAB) calculated for C34H45N3O4+H=560.3488, found=560.3487.

Workup

  1. customDichloromethane is then removed under reduced pressure
  2. customThe residue is partitioned between ethyl acetate and water
  3. customThe organic phase is separated
  4. washis washed with saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-59ea93867cc94be5a08d2acdf16e37db
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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