Ammonium Chloride → HCID 70975872, compound

HRID 455276Notes

Reaction equation

HRID 455276 reaction equation
[F:1][C:2]([F:40])([F:39])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([N:14]2[CH2:18][C@@H:17]([O:19][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][C@@H:15]2[CH2:37]O)=[O:13])=[CH:7][CH:6]=1.S(Cl)(C)(=O)=O.CC([O-])(C)C.[K+].[NH4+].[Cl-]>C(Cl)Cl>[C:33]([Si:20]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[O:19][C@@H:17]1[CH2:18][N:14]2[C:12](=[O:13])[N:11]([C:8]3[CH:7]=[CH:6][C:5]([O:4][CH2:3][C:2]([F:40])([F:39])[F:1])=[CH:10][CH:9]=3)[CH2:37][C@H:15]2[CH2:16]1)([CH3:34])([CH3:35])[CH3:36]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 71020561HCID 71020561, compound

Product 1

HCID 70975872HCID 70975872, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of (2R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid [4-(2,2,2-trifluoro-ethoxy)-phenyl]-amide (400 mg, 0.699 mmol) in DCM (5 mL) was added TEA (0.14 mL, 1.048 mmol) followed by mesylchloride (0.07 mL, 1.048 mmol) at 0° C. and stirred at room temperature for 12 h. DCM was added, the organic layer was washed with water and brine, dried over Na2SO4 and concentrated to dryness. 400 mg of the residue was taken up in THF (5 mL), t-BuOK (91 mg, 0.813 mmol) was added and the mixture was stirred for 1 h at room temperature. NH4Cl aq. and DCM was added. The organic layer was washed with water and brine, dried over Na2SO4. The residue was purified through column chromatography over silica (elution with 10% ethyl acetate in hexane) to afford (6S,7aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2-[4-(2,2,2-trifluoro-ethoxy)-phenyl]-hexahydro-pyrrolo[1,2-c]imidazol-3-one as an off white solid.

Workup

  1. washthe organic layer was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to dryness
  4. stirringthe mixture was stirred for 1 h at room temperature
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. customThe residue was purified through column chromatography over silica (elution with 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-11ed7eb27259432380fd8b02824bbd73
Source dataset
uspto-grants-2013_07
Patent number
US08497288B2

Reaction notes

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