Ethanol → HCID 69692805, compound

HRID 1814386Notes

Reaction equation

HRID 1814386 reaction equation
[C:1]([O:5][C:6](=[O:43])[CH2:7][C@H:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:34])[CH2:28][CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])=[CH:22][C:21]=1[O:35]CC1C=CC=CC=1)(=[O:19])=[O:18])[CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].CCO>[Pd].C1COCC1.CCO>[C:1]([O:5][C:6](=[O:43])[CH2:7][C@H:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:34])[CH2:28][CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])=[CH:22][C:21]=1[OH:35])(=[O:19])=[O:18])[CH:9]([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 702EthanolHCID 69692475HCID 69692475, compound

Product 1

HCID 69692805HCID 69692805, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

(S)-3-[2-Benzyloxy-4-(4-dimethylamino-butanoylamino)-benzenesulfonylamino]-4,4-diethoxy-butyric acid tert-butyl ester (0.62 g, 1.0 mmol) was shaken with 20% palladium on carbon (0.06 g) in THF-EtOH (1:1) under H2 (50 psi) for 16 h using a Parr apparatus. Mass spectrometry and NMR analysis indicated only starting material to be present. An additional 0.28 g of 20% Pd/C and EtOH (50 mL) were added and allowed to stir for 19.5 h. TLC analysis showed complete consumption of starting material. The reaction mixture was filtered through celite and concentrated to yield (S)-3-[4-(4-dimethylamino-butanoylamino)-2-hydroxy-benzensulfonylamino]-4,4-diethoxy-butyric acid tert-butyl ester (0.44 g, 0.83 mmol, 83%). MS (APCI) m/z 532.4 (M+1).

Workup

  1. customconsumption of starting material
  2. filtrationThe reaction mixture was filtered through celite and
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0f662d81688d4926b730c0aec45abfac
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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