HCID 19705529, compound → HCID 19705509, compound

HRID 727582Notes

Reaction equation

HRID 727582 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][C:41]=1[F:42])[C:5]([NH:7][CH2:8][CH2:9][CH:10]([C:22]1([CH2:36][CH2:37][OH:38])[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]1=[O:35])[C:11]([NH:13][O:14]CC1C=CC=CC=1)=[O:12])=[O:6]>CCO>[F:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][C:41]=1[F:42])[C:5]([NH:7][CH2:8][CH2:9][CH:10]([C:22]1([CH2:36][CH2:37][OH:38])[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:23]1=[O:35])[C:11]([NH:13][OH:14])=[O:12])=[O:6]

Participants

3

Reactant 1

HCID 19705529HCID 19705529, compound

Product 1

HCID 19705509HCID 19705509, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of α-[2-[(3,4-difluorobenzoyl)amino]ethyl]-N-benzyloxy-3-(2-hydroxyethyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamide (117 mg, 0.202 mmol) is dissolved in EtOH (3 mL) and purged with N2. Pearlman's catalyst (10 mg) is added and the atmosphere is replaced with H2. After 6 hours, the mixture is filtered through celite, washing the residual solids with MeOH, EtOH, and CH2Cl2. The filtrate is concentrated and resubjected to the same procedure. The recovered material (99 mg) is purified by silica gel chromatography (8 g SG; 5, 10% MeOH/CHCl3) to give 45 mg of a white, amorphous solid. The solid is triturated with Et2O/hexane, filtered, and dried. This provides 39 mg (40%) of the title compound as a white, powdery solid (mp 135°-137° C.):

Workup

  1. custompurged with N2
  2. additionPearlman's catalyst (10 mg) is added
  3. filtrationthe mixture is filtered through celite
  4. washwashing the residual solids with MeOH, EtOH, and CH2Cl2
  5. concentrationThe filtrate is concentrated
  6. customThe recovered material (99 mg) is purified by silica gel chromatography (8 g SG; 5, 10% MeOH/CHCl3)
  7. customto give 45 mg of a white, amorphous solid
  8. customThe solid is triturated with Et2O/hexane
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-5df49d79975a449abe45918cdeac26e5
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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