HCID 66902631, compound → HCID 66902468, compound

HRID 2425036Notes

Reaction equation

HRID 2425036 reaction equation
[CH2:1]([O:3][C:4]([C@:6]1([NH:21]C(OC(C)(C)C)=O)[CH2:11][C@H:10]([O:12][C:13](=[O:15])[CH3:14])[C@@H:9]2[C@H:7]1[C@H:8]2[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:5])[CH3:2]>C(O)(C(F)(F)F)=O.ClCCl>[CH2:1]([O:3][C:4]([C@:6]1([NH2:21])[CH2:11][C@H:10]([O:12][C:13](=[O:15])[CH3:14])[C@@H:9]2[C@H:7]1[C@H:8]2[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 66902631HCID 66902631, compound

Product 1

HCID 66902468HCID 66902468, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Dissolve (1S,2S,4S,5R,6R)-4-acetyloxy-2-(tert-butoxycarbonyl)aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester (1.25 g, 3.13 mmol, Preparation 19) in a solution of 95% TFA in dichloromethane (60 mL) and stir under nitrogen at room temperature for 5 minutes. After this time remove the TFA/dichloromethane in vacuo. Dissolve the crude product in a suspension of NaHCO3 (1.00 g) in dichloromethane (50 mL) and stir for 30 minutes. Filter the suspension, wash with dichloromethane (3×25 mL), and concentrate in vacuo to afford 916 mg (98%) of the product as a yellow oil.

Workup

  1. customAfter this time remove the TFA/dichloromethane in vacuo
  2. dissolutionDissolve the crude product
  3. additionin a suspension of NaHCO3 (1.00 g) in dichloromethane (50 mL)
  4. stirringstir for 30 minutes
  5. filtrationFilter the suspension
  6. washwash with dichloromethane (3×25 mL)
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f06c63517ab9496fb8bf550803bf878d
Source dataset
uspto-grants-2011_06
Patent number
US07964632B2

Reaction notes

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