HCID 14557674, compound → HCID 14997129, compound

HRID 374313Notes

Reaction equation

HRID 374313 reaction equation
[CH2:1]([C@H:8]([CH2:20][C@@H:21]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:22]([OH:24])=[O:23])[C:9]([NH:11][C@H:12]([C:17]([OH:19])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.O.[Rh]>[CH:2]1([CH2:1][C@@H:8]([CH2:20][C@H:21]([CH2:25][CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)[C:22]([OH:24])=[O:23])[C:9]([NH:11][C@H:12]([C:17]([OH:19])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 1

HCID 14557674HCID 14557674, compound

Product 1

HCID 14997129HCID 14997129, compound

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of 0.5 g of N-[(S,S)-2,4-dibenzyl-4-carboxybutyryl]-(L)-leucine and 0.5 g of 5% Rh/C in 10 ml of ethanol and 10 ml of water is hydrogenated for 36 hours at 3 atmospheres pressure (50 psi). The mixture is filtered through celite and concentrated. The colorless oil is treated with 1.0N sodium hydroxide in methanol and concentrated to yield N-[(S,S)-2,4-di-(cyclohexylmethyl)-4-carboxybutyryl]-(L)-leucine.

Workup

  1. filtrationThe mixture is filtered through celite
  2. concentrationconcentrated
  3. additionThe colorless oil is treated with 1.0N sodium hydroxide in methanol
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7770a792a31f42fa958ff14950c97ab6
Source dataset
uspto-grants-1992_11
Patent number
US05166212

Reaction notes

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