L-Lysine → (R)-2-(9-chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid L-lysine salt

HRID 1526421Notes

Reaction equation

[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=3)[CH:7]=[CH:6][C:5]=2[N:4]2[CH2:27][CH2:28][C@H:29]([CH2:30][C:31]([OH:33])=[O:32])[C:3]=12.[NH2:34][C@H:35]([C:41]([OH:43])=[O:42])[CH2:36][CH2:37][CH2:38][CH2:39][NH2:40]>C(#N)C>[NH2:34][C@H:35]([C:41]([OH:43])=[O:42])[CH2:36][CH2:37][CH2:38][CH2:39][NH2:40].[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([C:23]([F:24])([F:25])[F:26])[CH:14]=3)[CH:7]=[CH:6][C:5]=2[N:4]2[CH2:27][CH2:28][C@H:29]([CH2:30][C:31]([OH:33])=[O:32])[C:3]=12

Participants

Conditions

Temperature: 70 °C

Procedure

(R)-2-(9-Chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid (2.0 g, 4.15 mmol) was dissolved in acetonitrile (66 mL) with heating (70° C., oil bath) and a 2.0 M aqueous L-lysine solution (2.075 mL, 4.15 mmol) was added. After addition, the oil bath was turned off, and the reaction was allowed to slowly cool to room temperature and stirred for 16 h. The white solid was collected by vacuum filtration to afford 2.365 grams of the desired (R)-2-(9-chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid L-lysine salt (91% yield).

Workup

additionAfter addition
temperatureto slowly cool to room temperature
filtrationThe white solid was collected by vacuum filtration

Sources & evidence

ORD record: ord-1a20ffe1eb8440d485b580d9c314a2ab
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085581B2

Reaction notes

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