(S)-3-(4-acetylamino-2-benzyloxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester → (S)-3-(4-acetylamino-2-hydroxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester

HRID 1814367Notes

Reaction equation

HRID 1814367 reaction equation
[C:1]([O:5][C:6](=[O:38])[CH2:7][C@H:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:29])[CH3:28])=[CH:22][C:21]=1[O:30]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].[H][H]>[Pd].O1CCCC1>[C:1]([O:5][C:6](=[O:38])[CH2:7][C@H:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:29])[CH3:28])=[CH:22][C:21]=1[OH:30])(=[O:19])=[O:18])[CH:9]([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 69692085(S)-3-(4-acetylamino-2-benzyloxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl esterHCID 178418361HCID 178418361, compound2×

Product 1

HCID 69692589(S)-3-(4-acetylamino-2-hydroxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl esterYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

11.4 g (20.7 mmol) (S)-3-(4-Acetylamino-2-benzyloxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester, 1 g 20% Pd/C, and 100 mL tetrahydrofuran was shaken under a 50 psi hydrogen atmosphere for 19 h. TLC analysis indicated incomplete reaction, so an additional 1 g 20% Pd/C was added and the reaction shaken an additional 20 h under a 50 psig hydrogen atmosphere. TLC showed complete reaction. The catalyst was filtered and the resulting solution was concentrated to give an oil. The product was purified over silica eluting with ethyl acetate to yield 9.37 g (20.34 mmol, 98.3%) of (S)-3-(4-acetylamino-2-hydroxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester as an ivory-yellow solid. MS (APCI) m/z 459.1 (M−1).

Workup

  1. customreaction
  2. customreaction
  3. filtrationThe catalyst was filtered
  4. concentrationthe resulting solution was concentrated
  5. customto give an oil
  6. customThe product was purified over silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-0ad54c53922441a49aa7bcdecc6e896e
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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