Ethyl Acetate → HCID 9939117, compound

HRID 489580Notes

Reaction equation

HRID 489580 reaction equation
[CH3:1][N:2]([CH2:34][C@H:35]([OH:44])[C@@H:36]([OH:43])[C@H:37]([OH:42])[C@H:38]([OH:41])[CH2:39][OH:40])[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19](=[O:33])[C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=4)=[C:22]([CH3:32])[CH:21]=3)[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].C(N(CC)C(C)C)(C)C.[C:54](OCC)(=[O:56])C>ClCCl>[C:26]1([C:23]2[CH:24]=[CH:25][C:20]([C:19]([N:10]3[C:11]4[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=4[CH2:13][N:14]4[C:5]([C:3]([N:2]([CH2:34][C@@H:35]([C@@H:36]5[C@@H:37]([C@H:38]([OH:41])[CH2:39][OH:40])[O:42][C:54](=[O:56])[O:43]5)[OH:44])[CH3:1])=[O:4])=[CH:6][CH:7]=[C:8]4[CH2:9]3)=[O:33])=[CH:21][C:22]=2[CH3:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 69797317HCID 69797317, compound

Product 1

HCID 9939117HCID 9939117, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

10-(4-Cyclohex-1-en-1-yl-3-methyl-benzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid methyl-[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxy-hexyl]-amide of Example 5 (0.190 g, 0.315 mmol), and N,N-diisopropylethylamine (0.110 mL, 0.315 mmol) were dissolved in anhydrous dichloromethane (6.3 mL) and the solution cooled to 0° C. N,N′-Carbonyldiimidazole (0.051 g, 0.315 mmol) was added and the reaction stirred at 0° C. for 1 hour, then warmed to room temperature and stirring continued for 12 hours. The solution was diluted with ethyl acetate and washed with water, 0.1 N hydrochloric acid and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated. Purification of the residue by flash column chromatography on silica gel eluting with ethyl acetate, afforded 0.140 g of the title compound as a white, partially crystalline solid, m.p. 166-175° C.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirring
  3. waitcontinued for 12 hours
  4. washwashed with water, 0.1 N hydrochloric acid and brine
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue by flash column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-07de07c313904b2f93d7ab2ff95afdc9
Source dataset
uspto-grants-2005_12
Patent number
US06977254B2

Reaction notes

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