HCID 57562539, compound → HCID 57562519, compound

HRID 1725624Notes

Reaction equation

HRID 1725624 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:23]([O:25][CH3:26])=[O:24])[CH2:10][S:11][CH:12]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:13][N+:14]([O-])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)(=O)C>[NH2:14][CH2:13][CH:12]([S:11][CH2:10][C@H:9]([C:23]([O:25][CH3:26])=[O:24])[NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 57562539HCID 57562539, compound

Product 1

HCID 57562519HCID 57562519, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

10% palladium on carbon (3.04 g) was added to a solution of methyl N-(tert-butoxycarbonyl)-S-(2-nitro-1-phenylethyl)-D-cysteinate (1.00 g, 2.60 mmol) in acetic acid (50 mL). The reaction vessel was evacuated and back-filled with nitrogen (3×), then back-filled with hydrogen (50 psi). After 18 h the mixture was filtered, concentrated, and saturated aqueous sodium carbonate was added. The mixture was extracted with dichloromethane (3×), and the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated to give the title compound (0.73 g). MS 355 (M+1).

Workup

  1. customThe reaction vessel was evacuated
  2. additionback-filled with nitrogen (3×)
  3. additionback-filled with hydrogen (50 psi)
  4. filtrationAfter 18 h the mixture was filtered
  5. concentrationconcentrated
  6. additionsaturated aqueous sodium carbonate was added
  7. extractionThe mixture was extracted with dichloromethane (3×)
  8. dry with materialthe combined organic extracts were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-5919f68c4b8e490f9340942f21ef0329
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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