Benzoyl chloride → HCID 70080082, compound

HRID 1489797Notes

Reaction equation

HRID 1489797 reaction equation
[C:1]1([NH:7][C:8](=[O:53])[C@H:9]([CH2:49][CH:50]([CH3:52])[CH3:51])[N:10]([CH2:22][P@:23]([O:47][CH3:48])([CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30](=[O:46])[C@@H:31]2[CH2:35][CH2:34][CH2:33][N:32]2[C:36](OCC2C=CC=CC=2)=[O:37])=[O:24])[C:11](=[O:21])[CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1.CN1CCOCC1>CO.C(OCC)(=O)C.O.[Pd]>[C:1]1([NH:7][C:8](=[O:53])[C@H:9]([CH2:49][CH:50]([CH3:52])[CH3:51])[N:10]([CH2:22][P@:23]([O:47][CH3:48])([CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30](=[O:46])[C@@H:31]2[CH2:35][CH2:34][CH2:33][N:32]2[C:36](=[O:37])[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[O:24])[C:11](=[O:21])[CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 7412Benzoyl chlorideHCID 79724-MethylmorpholineHCID 70078497HCID 70078497, compound

Product 1

HCID 70080082HCID 70080082, compound

Reagents, catalysts & solvents 3

HCID 23219155Palladium hydrateCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of [[(R,S)-methoxy-[N-(N-(benzyloxycarbonyl)-L-prolyl)aminobutyl]phosphinyl]methyl]-4-phenylbutanoyl-L-leucine N-phenylamide (169 mg, 0.226 mmol) in methanol (2 mL) was stirred for 6 hours under an atmosphere of hydrogen in the presence of 20% palladium hydroxide-on-carbon (34 mg). The catalyst was removed by filtration through Celite, the filter washed with methanol, and the combined filtrate and washings evaporated. The resulting amine was dried under high vacuum, then dissolved in methylene chloride (2 mL), cooled to 0° C. and treated with benzoyl chloride (29 ml, 0.25 mmol) and N-methylmorpholine (27 μl, 0.25 mmol) at 0° C. for 90 min. The reaction mixture was diluted with ethyl acetate (25 mL), washed with 2N hydrochloric acid, saturated brine solution, dried (magnesium sulfate), and evaporated. Purification was achieved by flash chromatography on silica gel using initially 2% methanol in methylene chloride and subsequently 3% methanol in methylene chloride; yield 101 mg (62%); FAB MS: m/z 716 (M+1).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. washthe filter washed with methanol
  3. customthe combined filtrate and washings evaporated
  4. dry with materialThe resulting amine was dried under high vacuum
  5. dissolutiondissolved in methylene chloride (2 mL)
  6. washwashed with 2N hydrochloric acid, saturated brine solution
  7. dry with materialdried (magnesium sulfate)
  8. customevaporated
  9. customPurification

Sources & evidence

ORD record
ord-1cc5fd09f18a4c43b26d840f97c4d24c
Source dataset
uspto-grants-1997_10
Patent number
US05679700

Reaction notes

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