Acetic Anhydride → {2-[4-Acetyl-6-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-1-cyclohexyl-2-oxo-ethyl}-carbamic acid tert-butyl ester

HRID 1949647Notes

Reaction equation

HRID 1949647 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][CH:8]([CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[C:9]([N:11]1[CH2:15][CH2:14][CH:13]2[NH:16][CH2:17][CH:18]([C:19]3[C:27]4[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[CH:12]12)=[O:10])([CH3:4])([CH3:3])[CH3:2].[CH3:36][C:37](OC(C)=O)=[O:38]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:35])[NH:7][CH:8]([CH:29]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1)[C:9]([N:11]1[CH2:15][CH2:14][CH:13]2[N:16]([C:37](=[O:38])[CH3:36])[CH2:17][CH:18]([C:19]3[C:27]4[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[CH:12]12)=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 67410158HCID 67410158, compound

Product 1

HCID 67410100{2-[4-Acetyl-6-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-1-cyclohexyl-2-oxo-ethyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution containing 49 (200 mg, 0.41 mmol) in DCM (5 mL) was added Ac2O (65 mg, 0.63 mmol) and DMAP (5 mg, cat.) at ambient temperature. After 16 h, the reaction mixture was diluted with DCM, washed successively with 1M HCl and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 170 mg (78%) of crude 68 which was used without further purification. Mass spectrum, m/z [527] (M+H)+.

Workup

  1. washwashed successively with 1M HCl and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford 170 mg (78%) of crude 68 which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-64b135ce4d6f400f8abfdb9f003f800f
Source dataset
uspto-grants-2013_03
Patent number
US08399683B2

Reaction notes

Loading…