HCID 19705517, compound → HCID 19705568, compound

HRID 727579Notes

Reaction equation

HRID 727579 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:40]=[CH:41][C:42]=1[F:43])[C:5]([NH:7][CH2:8][CH2:9][CH:10]([C:22]1([CH2:36][CH2:37][CH2:38][OH:39])[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:40]=[CH:41][C:42]=1[F:43])[C:5]([NH:7][CH2:8][CH2:9][CH:10]([C:22]1([CH2:36][CH2:37][CH2:38][OH:39])[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 19705517HCID 19705517, compound

Product 1

HCID 19705568HCID 19705568, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of α-[2-[(3,4-difluorobenzoyl)amino]ethyl]-N-benzyloxy-3-(3-hydroxypropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamide (215 mg, 0.368 mmol) is dissolved in EtOH (5 mL) and purged with N2. Pearlman's catalyst (22 mg) is added and the atmosphere was replaced with H2 . After 7 hours, the mixture is filtered through celite, washing the residual solids with MeOH, EtOH, and CH2Cl2. The filtrate is concentrated to give 171 mg of a slightly brown foam. The material is crystallized from hot EtOAc (diluting with hexane). The product is isolated and dried in the vacuum oven (45° C.) overnight to provide 117 mg (63%) of the title compound as a cream-colored, powdery solid (mp 118° C., dec.):

Workup

  1. custompurged with N2
  2. additionPearlman's catalyst (22 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. customto give 171 mg of a slightly brown foam
  7. customThe material is crystallized from hot EtOAc (diluting with hexane)
  8. customThe product is isolated
  9. customdried in the vacuum oven (45° C.) overnight

Sources & evidence

ORD record
ord-35c0c235aeb84e4cb775415c4184cc9d
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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