HCID 131721328, compound → HCID 131721327, compound

HRID 1584249Notes

Reaction equation

HRID 1584249 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([C:23]([OH:25])=[O:24])[CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])[CH3:3].C([O:33][C:34](=[O:40])[C@@H:35]1[CH2:39][CH2:38][CH2:37][NH:36]1)C1C=CC=CC=1>C(O)C.[Pd]>[CH3:4][C:2]([O:5][C:6]([NH:8][C@@H:9]([C:23]([OH:25])=[O:24])[CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:1])[CH3:3].[NH:36]1[CH2:37][CH2:38][CH2:39][C@H:35]1[C:34]([OH:40])=[O:33]

Participants

4

Reactant 1

HCID 131721328HCID 131721328, compound

Product 1

HCID 131721327HCID 131721327, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of Boc-D-3,3-diphenylalanine-L-proline benzyl ester (8.0 g, 15.0 mmol) in ethanol (200 ml) was hydrogenated in the presence of 10% Pd/C (2.0 g) a t atmospheric pressure for 24 h. The reaction mixture was then filtered through Celite and the filtrate concentrated in vacuo to give the title compound as a white solid: 1H NMR (CDCl3) d 1.20-1.40 (m, 1 H), 1.35 (s, 9 H), 1.40-1.60 (m, 1 H), 1.70-1.90 (m, 1 H), 2.21-2.30 (m, 1 H), 2.70 (q, J=9 Hz, 1 H), 3.75 (br t, J=9 Hz, 1 H), 4.16 (d, J=9 Hz, 1 H), 4.35 (d, J=11.5 Hz, 1 H), 4.97-5.18 (m, 2 H), 7.22-7.39 (m, 10 H).

Workup

  1. customfor 24 h
  2. filtrationThe reaction mixture was then filtered through Celite
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-5105f45a827144ec9738b7bba9c3958e
Source dataset
uspto-grants-1999_08
Patent number
US05932606

Reaction notes

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