Cesium carbonate → HCID 57968585, compound

HRID 882758Notes

Reaction equation

HRID 882758 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:22][CH2:21][CH2:20][N:19]([CH:23]2[CH2:26][CH2:25][CH2:24]2)[CH2:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].I[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CC1C=NC2C(C=1C)=CC=C1C=2N=CC(C)=C1C.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:22][CH2:21][CH2:20][N:19]([CH:23]2[CH2:24][CH2:25][CH2:26]2)[CH2:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 44600522HCID 44600522, compound

Product 1

HCID 57968585HCID 57968585, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred suspension of (2S,4R)-2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (116 mg, 0.32 mmol) in toluene (0.65 ml) was added iodobenzene (129 mg, 0.63 mmol), copper (I) iodide (6 mg, 0.032 mmol), 3,4,7,8-tetramethyl-1,10-phenanthroline (15 mg, 0.063 mmol), and Cs2CO3 (206 mg, 0.63 mmol). The resulting suspension was heated at 100° C. in a capped scintillation vial with stirring for 2 days. The reaction mixture was filtered through diatomaceous earth, washing with CH2Cl2. The filtrate was dried and concentrated. Purification of the residue by FCC provided the desired product (97.7 mg, 70%). MS (ESI): mass calcd. for C25H37N3O4, 443.3; m/z found, 444.3 [M+H]+. 1H NMR (CDCl3): 7.30-7.25 (m, 2H), 6.96 (dd, J=14.5, 7.2 Hz, 1H), 6.85 (dd, J=7.7, 5.5 Hz, 1H), 5.04-4.91 (m, 1H), 4.88-4.71 (m, 1H), 3.89-3.43 (m, 6H), 2.92-2.79 (m, 1H), 2.70-2.20 (m, 6H), 2.07-1.74 (m, 7H), 1.71-1.52 (m, 2H), 1.43-1.41 (m, 9H).

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washwashing with CH2Cl2
  3. customThe filtrate was dried
  4. concentrationconcentrated
  5. customPurification of the residue by FCC

Sources & evidence

ORD record
ord-eefb40f298aa4e079c590b6fb5d015d9
Source dataset
uspto-grants-2012_08
Patent number
US08236792B2

Reaction notes

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