N-Methyl-D-glucamine → (R)-2-(9-chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid N-methylglucamine salt

HRID 1526427Notes

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.[CH3:34][NH:35][CH2:36][C@@H:37]([C@H:39]([C@@H:41]([C@@H:43]([CH2:45][OH:46])[OH:44])[OH:42])[OH:40])[OH:38]>CC(C)=O>[CH3:34][NH:35][CH2:36][C@@H:37]([C@H:39]([C@@H:41]([C@@H:43]([CH2:45][OH:46])[OH:44])[OH:42])[OH:40])[OH:38].[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: 50 °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 (15 mg, 0.0311 mmol) was dissolved in acetone (0.5 mL) and warmed to 50° C. Aqueous N-methylglucamine (14 uL, 2.27M) was added and the mixture was allowed to slowly cool to 30° C. over 24 h. The reaction mixture was evaporated to dryness, and EtOAc (0.5 mL) was added to provide a solid which was collected by filtration.

Workup

temperatureto slowly cool to 30° C. over 24 h
customThe reaction mixture was evaporated to dryness, and EtOAc (0.5 mL)
additionwas added
customto provide a solid which
filtrationwas collected by filtration

Sources & evidence

ORD record: ord-79a6ebd51e3f4b17a7fb05440a1d296a
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085581B2

Reaction notes

Loading…