Water → HCID 9939901, compound

HRID 1872818Notes

Reaction equation

HRID 1872818 reaction equation
C([O:8][C:9]([CH2:11][CH2:12][CH2:13][C@H:14]([NH:37][C:38](=[O:56])[CH2:39][C@@H:40]([OH:55])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH:52]([CH3:54])[CH3:53])[C:15]([O:17][C@@H:18]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH2:19][C:20]([NH2:22])=[O:21])=[O:16])=[O:10])C1C=CC=CC=1.O>O1CCOCC1.CO.[Pd]>[C:9]([CH2:11][CH2:12][CH2:13][C@H:14]([NH:37][C:38](=[O:56])[CH2:39][C@@H:40]([OH:55])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH:52]([CH3:54])[CH3:53])[C:15]([O:17][C@@H:18]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH:34]([CH3:35])[CH3:36])[CH2:19][C:20]([NH2:22])=[O:21])=[O:16])([OH:10])=[O:8]

Participants

6

Reactant 2

HCID 962WaterHCID 10533287HCID 10533287, compound

Product 1

HCID 9939901HCID 9939901, compoundYield 79.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (3S)-3-[(2S)-5-benzyloxycarbonyl-2-{(3S)-3-hydroxy-15-methylhexadecanoylamino}pentanoyl]oxy-15-methylhexadecanamide (80 mg) in a mixture of 1,4-dioxane (10 ml) and methanol (10 ml) were added 10% palladium on active carbon (50 mg) and water (1 ml). The mixture was stirred at room temperature under hydrogen atmosphere for 1 hour. The catalyst was filtered off and the solvent was removed under reduced pressure to give (3S)-3-[(2S)-5-carboxy-2-{(3S)-3-hydroxy-15-methylhexadecanoylamino}-pentanoyl]oxy-15-methylhexadecanamide as white powder (56 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e1a1c76c8689434db5b5bb3391a73821
Source dataset
uspto-grants-2000_08
Patent number
US06110933

Reaction notes

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