Water → HCID 54282592, compound

HRID 1532353Notes

Reaction equation

[C:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([CH2:15][CH2:16][C@@H:17]3[CH2:21][CH2:20][CH2:19][N:18]3[C:22]([C@H:24]3[CH2:28][CH2:27][CH2:26][N:25]3[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:23])[N:10]2[CH2:13][CH3:14])=[CH:6][CH:5]=1)(=[NH:3])N.[CH2:35]([N:37](CC)CC)[CH3:36].C(Cl)(=[O:44])C.O>ClCCl>[CH2:13]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([CH:1]=[N:3][NH:37][C:35](=[O:44])[CH3:36])[CH:12]=2)[CH:8]=[C:9]1[CH2:15][CH2:16][C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:22]([C@H:24]1[CH2:28][CH2:27][CH2:26][N:25]1[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:23])[CH3:14]

Participants

Conditions

Temperature: -78 °C

Procedure

52 mg of ethyl 2-[(R)-2-[[(S)-2-[2-(6-amidino-1-ethylindol-2-yl)ethyl]pyrrolidinyl]carbonyl]pyrrolidinyl]acetate obtained in Example 60 was dissolved in dry dichloromethane. To the resulting solution was added 31 μl of triethylamine, and the mixture was cooled to −78° C. After 16 μl of acetyl chloride was added, the reaction solution was stirred for 3 hours and warmed to room temperature. Water was added and the mixture was extracted with dichloromethane. The extract was dried over MgSO4 and evaporated under reduced pressure to remove the solvent. The residue was purified with silica gel column chromatography [eluent: ethyl acetate/methanol(50:1)] to obtain 7 mg of the title compound as a pale yellow solid.

Workup

temperaturewarmed to room temperature
extractionthe mixture was extracted with dichloromethane
dry with materialThe extract was dried over MgSO4
customevaporated under reduced pressure
customto remove the solvent
customThe residue was purified with silica gel column chromatography [eluent: ethyl acetate/methanol(50:1)]

Sources & evidence

ORD record: ord-baf95a1ba62f4868b0e54e3483385d9c
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06201006B1

Reaction notes

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