1,2-Dichloroethane → HCID 21086265, compound

HRID 348833Notes

Reaction equation

HRID 348833 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11](=[O:16])[CH2:12][CH2:13][CH2:14][CH3:15])[CH:10]=1)[C:5]([OH:7])=O.FC(F)(F)C(O)=O.[NH2:24][C@@H:25]([CH2:39][C:40]1[CH:45]=[C:44]([F:46])[CH:43]=[C:42]([F:47])[CH:41]=1)[C@H:26]([OH:38])[CH2:27][NH:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>C(Cl)Cl>[F:46][C:44]1[CH:45]=[C:40]([CH:41]=[C:42]([F:47])[CH:43]=1)[CH2:39][C@@H:25]([NH:24][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([C:11](=[O:16])[CH2:12][CH2:13][CH2:14][CH3:15])[CH:10]=[C:2]([CH3:1])[CH:3]=1)[C@H:26]([OH:38])[CH2:27][NH:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 210858393-Methyl-5-pentanoylbenzoic acidHCID 69869154(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol Trifluoroacetate

Product 1

HCID 21086265HCID 21086265, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-methyl-5-pentanoylbenzoic acid (IX–LXXVII, 112 mg, 0.589 mmol), (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol dihydrochloride (VIII, 239 mg, 0.589 mmol), HOBt (80 mg, 0.589 mmol), and N-methylmorpholine (250 mg, 2.47 mmol) in methylene chloride (3 mL) is added EDC (203 mg, 1.06 mmol). The reaction mixture is stirred overnight and then partitioned between ethyl acetate and water. The organic phase is washed with hydrochloric acid (1 N), saturated sodium bicarbonate, saline, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica; methylene chloride/methanol, 12/1) gives the title compound, IR (ATR): 3297, 2957, 1687 and 1628 cm−1; APCI-MS (m/z) [M+H]+=539.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase is washed with hydrochloric acid (1 N), saturated sodium bicarbonate, saline
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography (silica; methylene chloride/methanol, 12/1)

Sources & evidence

ORD record
ord-3c854cbace674e739e1e7cbd18f43ffc
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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