Acetic Anhydride → HCID 58294655, compound

HRID 2360803Notes

Reaction equation

HRID 2360803 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 7:3→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 7:3→1:9)

Sources & evidence

ORD record
ord-ad98ee13383c4383818aed079f5e0f2d
Source dataset
uspto-grants-2014_04
Patent number
US08686149B2

Reaction notes

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