Dicyclohexylcarbodiimide → bis-Boc-L-Ornithyl-D-Homophenylalanine Benzyl ester

HRID 1365887Notes

Reaction equation

HRID 1365887 reaction equation
[CH2:1]([O:8][C:9](=[O:20])[C@@H:10]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([N:28]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:29]([C:34](O)=[O:35])[CH2:30][CH2:31][CH2:32][NH2:33])([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C.ON1C(=O)CCC1=O>[CH2:1]([O:8][C:9](=[O:20])[C@@H:10]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:11][C:34](=[O:35])[C@H:29]([CH2:30][CH2:31][CH2:32][NH2:33])[N:28]([C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])[C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 15630399D-Homophenylalanine Benzyl esterHCID 18638603Di-boc-ornithine

Product 1

HCID 86602420bis-Boc-L-Ornithyl-D-Homophenylalanine Benzyl ester

Reagents, catalysts & solvents 2

HCID 80170N-HydroxysuccinimideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

D-Homophenylalanine Benzyl ester Tosylate (2.48 g, 5.6 mmol) was suspended in ethyl acetate (25 mL) and a saturated solution of sodium bicarbonate in water was added in portions (25 mL) with stirring at 25° C. The water layer was extracted with ethyl acetate (3×10 mL). The combined organic extract was dried over anhydrous sodium sulfate, filtered and concentrated to dryness to afford D-Homophenylalanine Benzyl ester. The ester was dissolved in acetonitile (25 mL). NaNd-bis-Boc-L-Ornithine (2.0 g, 6.0 mmol) was then added followed by N-hydroxysuccinimide (50 mg) and dicyclohexylcarbodiimide (1.28 g, 6.2 mmol). The reaction was stirred at 25° C. for 30 hr, filtered and the filtrate concentrated to dryness to afford crude product. It was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1), which gave the title product (2.80 g) as white solid.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated to dryness
  3. customto afford crude product
  4. customIt was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1), which

Sources & evidence

ORD record
ord-38082d137423430c980a108784e71543
Source dataset
uspto-grants-2011_02
Patent number
US07893020B2

Reaction notes

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