Triethylamine → HCID 86758388, compound

HRID 2231091Notes

Reaction equation

HRID 2231091 reaction equation
[C:1]([O:5][C:6](=[O:27])[CH2:7][N:8]1[C:14](=[O:15])[CH:13]([N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[CH2:12][CH2:11][CH2:10][NH:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>ClCCl>[C:1]([O:5][C:6](=[O:27])[CH2:7][N:8]1[C:14](=[O:15])[CH:13]([N:16]2[C:17](=[O:26])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]2=[O:25])[CH2:12][CH2:11][CH2:10][N:9]1[S:36]([CH3:35])(=[O:38])=[O:37])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53762810HCID 53762810, compound

Product 1

HCID 86758388HCID 86758388, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of [6-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-7-oxo-[1,2]diazepan-1-yl]-acetic acid tert-butyl ester (21) (155 mg, 0.42 mmol), triethylamine (0.5 mL) and 4-N,N-dimethylaminopyridine (DMAP) (101 mg, 0.50 mmol) in dichloromethane was added dropwise methanesulfonyl chloride (95 mg, 0.83 mmol). The mixture was stirred at 0° C. for 5 min then at room temperature for 16 hours. The mixture was quenched with water, extracted with dichloromethane. The organic solution was washed with water then brine, dried over anhydrous Na2SO4, filtered and purified by flash chromatography using dichloromethane/ethyl acetate (99/1 to 95/5) to afford 154 mg (82% yield) of the title compound. 1H-NMR (500 MHz, CDCl3) δ 1.47 (s, 9H), 2.05-2.21 (m, 2H), 2.83-2.87 (m, 1H), 3.27 (s, 3H), 3.53-3.58 (m, 1H), 4.07-4.11 (d, 1H), 4.29-4.33 (m, 1H), 4.50-4.53 (d, 1H), 5.42-5.44 (m, 1H), 7.70-7.85 (m, 4H). Analytical HPLC: 12.27 min. LC-MS (ES+): m/e=452 (M+H+).

Workup

  1. waitat room temperature for 16 hours
  2. customThe mixture was quenched with water
  3. extractionextracted with dichloromethane
  4. washThe organic solution was washed with water
  5. dry with materialbrine, dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-3075c4926a1e43d991ed841079e99958
Source dataset
uspto-grants-2002_07
Patent number
US06426413B1

Reaction notes

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