Acetic Anhydride → HCID 58294655, compound

HRID 455373Notes

Reaction equation

HRID 455373 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH2:18][C@@H:17]2[C:21]3[CH:22]=[CH:23][C:24]([NH2:28])=[CH:25][C:26]=3[CH2:27][C@H:16]12)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>ClCCl>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH2:18][C@@H:17]2[C:21]3[CH:22]=[CH:23][C:24]([NH:28][C:1](=[O:3])[CH3:2])=[CH:25][C:26]=3[CH2:27][C@H:16]12)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 58294594HCID 58294594, compound

Product 1

HCID 58294655HCID 58294655, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (50 μL) is added to a solution of cis-7-amino-2,3,4,4a,9,9a-hexahydro-indeno[2,1-b]pyridine-1-carboxylic acid tert-butyl ester (140 mg) and triethylamine (70 μL) in dichloromethane (3 mL) at room temperature. The solution is stirred for 1 h at room temperature and then aqueous NaHCO3 solution is added. The mixture is stirred vigorously for 20 min and then extracted with dichloromethane. The combined extract is concentrated and the residue is chromatographed (cyclohexane/ethyl acetate 1:9) to give the title compound. Yield: 100 mg (62% of theory); LC (method 1): tR=3.60 min.

Workup

  1. stirringThe mixture is stirred vigorously for 20 min
  2. extractionextracted with dichloromethane
  3. extractionThe combined extract
  4. concentrationis concentrated
  5. customthe residue is chromatographed (cyclohexane/ethyl acetate 1:9)

Sources & evidence

ORD record
ord-22d17833295a4b1da0ceee41c5858390
Source dataset
uspto-grants-2013_07
Patent number
US08497281B2

Reaction notes

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