Trifluoroacetic acid → HCID 67231818, compound

HRID 2047460Notes

Reaction equation

HRID 2047460 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:24])/[CH:15]=[CH:16]/[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH2:27][N:28]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:29][Si](C)(C)C.FC(F)(F)C(O)=O>ClCCl.O>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([C@H:15]1[C@H:16]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]=2)[CH2:29][N:28]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:27]1)=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([C@@H:15]1[C@@H:16]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]=2)[CH2:29][N:28]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:27]1)=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 67232581HCID 67232581, compound

Product 2

HCID 67231818HCID 67231818, compoundHCID 67232677HCID 67232677, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound (8.26 g) obtained in step 4 in dichloromethane (100 mL) were added at room temperature N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (9.6 g) and trifluoroacetic acid (0.58 g), and the mixture was stirred at 18 hr. The mixture was diluted with water (200 mL), extracted with dichloromethane (2×200 mL), dried and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (25% ethyl acetate/hexane) to give (4R)-4-benzyl-3-{[(3S,4S)-1-benzyl-4-(5-fluoropyridin-2-yl)pyrrolidin-3-yl]carbonyl}-1,3-oxazolidin-2-one (less polar product, 11.8 g, 47%) as a yellow oil, and (4R)-4-benzyl-3-{[(3R,4R)-1-benzyl-4-(5-fluoropyridin-2-yl)pyrrolidin-3-yl]carbonyl}-1,3-oxazolidin-2-one (more polar product, 10.5 g, 41%) as a yellow oil.

Workup

  1. extractionextracted with dichloromethane (2×200 mL)
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was separated
  5. custompurified by silica gel column chromatography (25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6f4efc5bfb2a40c781e5d8d9a79b2dab
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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