Dichloromethane → HCID 68816253, compound

HRID 732599Notes

Reaction equation

HRID 732599 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[CH2:10][C@@H:9]1[C@@H:22]([OH:34])[C@@H:23]([NH2:33])[CH2:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CC[O:39][CH2:38][CH2:37]1.ClCCl>>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[CH2:10][C@@H:9]1[C@@H:22]([OH:34])[C@@H:23]([NH:33][C:38](=[O:39])[CH3:37])[CH2:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 79724-MethylmorpholineHCID 68815117HCID 68815117, compound

Product 1

HCID 68816253HCID 68816253, compoundYield 69%

Procedure

Add to an ice cold solution of (2R,4R)-2-[(1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-4-(3-methoxy-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.24 g, 0.51 mmol) and 4-methylmorpholine (0.061 mL, 0.556 mmol) in dichloromethane (15 mL) 1-acetylimidazole (0.061 g, 0.556 mmol). Warm to room temperature and stir 18 h. Concentrate and dissolve in ethyl acetate and wash with 1N HCl, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dry (magnesium sulfate) and purify (silica gel chromatography, eluting with dichloromethane/ethyl acetate mixtures) to give the title compound as a foam (0.18 g, 69%).

Workup

  1. concentrationConcentrate
  2. dissolutiondissolve in ethyl acetate
  3. washwash with 1N HCl, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. custompurify
  6. wash(silica gel chromatography, eluting with dichloromethane/ethyl acetate mixtures)

Sources & evidence

ORD record
ord-c07c856f1b554e8c927d62f3936dbe48
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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