Diisopropylethylamine → HCID 68818763, compound

HRID 736771Notes

Reaction equation

HRID 736771 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH:10]([NH2:11])[CH:9]2[N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]1[CH2:7][CH2:8]2)=[O:4].Cl.[CH3:21][C:22]1[CH:31]=[C:30]([CH2:32][O:33][C:34]2[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=2)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:1][O:2][C:3]([CH:5]1[CH:10]([NH:11][S:40]([C:37]2[CH:38]=[CH:39][C:34]([O:33][CH2:32][C:30]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=[C:22]([CH3:21])[CH:31]=3)=[CH:35][CH:36]=2)(=[O:41])=[O:42])[CH:9]2[N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]1[CH2:7][CH2:8]2)=[O:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 688178247-(1,1-Dimethylethyl) 2-methyl 3-amino-7-azabicyclo[2.2.1]heptane-2,7-dicarboxylateHCID 866078654-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride

Product 1

HCID 68818763HCID 68818763, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 3-amino-7-aza-bicyclo[2.2.1]heptane-2,7-dicarboxylic acid 7-tert-butyl ester 2-methyl ester (0.2 g, 0.87 mmol] and 4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride (0.4 g, 1.0 mmol) in N,N-dimethylformamide (DMF, 10 mL) at 0° C. was added N,N-diisopropylethylamine (0.4 mL, 2.23 mmol). The solution was allowed to warm up to 25° C. over 19 h. The DMF was removed in vacuo and the solid was partitioned between ethyl acetate (100 mL) and water (30 mL). The aqueous layer was washed with ethyl acetate (2×50 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified on a Biotage Flash 40S chromatography, eluting with 1:4 ethyl acetate-hexanes, to afford 3-[4-(2-methyl-quinolin-4-ylmethoxy)-benzene sulfonylamino]-7-aza-bicyclo [2.2.1]heptane-2,7-dicarboxylic acid 7-tert-butyl ester-2-methyl ester as a white solid (0.150 g, 23.5%). MS: 582 (M+H)+.

Workup

  1. customThe DMF was removed in vacuo
  2. customthe solid was partitioned between ethyl acetate (100 mL) and water (30 mL)
  3. washThe aqueous layer was washed with ethyl acetate (2×50 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on a Biotage Flash 40S chromatography
  8. washeluting with 1:4 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-04dd5617d3134d4bb9d4e820ea513f18
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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