Benzyl [(1S)-1-[(benzyloxy)methyl]-2-({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-2-oxoethyl]carbamate → tert-Butyl {(4S)-5-{[(2S)-2-amino-3-hydroxypropanoyl]amino}-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate

HRID 269649Notes

Reaction equation

HRID 269649 reaction equation
C(OC(=O)[NH:10][C@@H:11]([CH2:36][O:37]CC1C=CC=CC=1)[C:12]([NH:14][CH2:15][C@@H:16]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:13])C1C=CC=CC=1>C(O)C.[Pd]>[C:24]([O:23][C:21](=[O:22])[NH:20][CH2:19][CH2:18][CH2:17][C@H:16]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:15][NH:14][C:12](=[O:13])[C@@H:11]([NH2:10])[CH2:36][OH:37])([CH3:27])([CH3:26])[CH3:25]

Participants

4

Reactant 1

HCID 86624498Benzyl [(1S)-1-[(benzyloxy)methyl]-2-({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-2-oxoethyl]carbamate

Product 1

HCID 86624499tert-Butyl {(4S)-5-{[(2S)-2-amino-3-hydroxypropanoyl]amino}-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 128 mg (0.77 mmol) of benzyl[(1S)-1-[(benzyloxy)methyl]-2-({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-2-oxoethyl]carbamate (Example 127A) in 50 ml of ethanol is hydrogenated after the addition of 13 mg of palladium on activated carbon (10%) at RT under atmospheric pressure for 48 h. The mixture is filtered through kieselguhr and the residue is washed with ethanol. The filtrate is evaporated to dryness in vacuo. The product is purified by preparative RP-HPLC (mobile phase water/acetonitrile gradient: 90:10→5:95).

Workup

  1. filtrationThe mixture is filtered through kieselguhr
  2. washthe residue is washed with ethanol
  3. customThe filtrate is evaporated to dryness in vacuo
  4. customThe product is purified by preparative RP-HPLC (mobile phase water/acetonitrile gradient: 90:10→5:95)

Sources & evidence

ORD record
ord-876ba323db0d43f6964dda67fc285e1c
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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