Citric Acid → HCID 66902631, compound

HRID 2242291Notes

Reaction equation

HRID 2242291 reaction equation
[CH2:1]([O:3][C:4]([C@:6]1([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:11][C@H:10]([OH:12])[C@@H:9]2[C@H:7]1[C@H:8]2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:5])[CH3:2].N1C=CC=CC=1.[C:32](OC(=O)C)(=[O:34])[CH3:33].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C1C=CN=CC=1)C.ClCCl>[CH2:1]([O:3][C:4]([C@:6]1([NH:18][C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:11][C@H:10]([O:12][C:32](=[O:34])[CH3:33])[C@@H:9]2[C@H:7]1[C@H:8]2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 15479118HCID 15479118, compound

Product 1

HCID 66902631HCID 66902631, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (1S,2S,4S,5R,6R)-2-(tert-butoxycarbonyl)amino-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester (1.50 g, 4.20 mmol, U.S. Pat. No. 5,958,960), pyridine (0.365 mL, 4.62 mmol) and DMAP (0.513 g, 4.20 mmol) in dichloromethane (40 mL) under nitrogen add acetic anhydride (0.514 mL, 5.0 mmol). Stir at room temperature for 16 hours, dilute with dichloromethane, and pour into 10% aqueous citric acid solution (50 mL). Wash the organic layer with water (50 mL) and brine (50 mL). Dry over MgSO4, filter and concentrate in vacuo, to produce the title compound as a white solid (1.295 g, 75%).

Workup

  1. washWash the organic layer with water (50 mL) and brine (50 mL)
  2. dry with materialDry over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-0a6a401e0ba345bf9b4c157ff7772447
Source dataset
uspto-grants-2010_03
Patent number
US07671082B2

Reaction notes

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