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

HRID 1526426Notes

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.[Zn:34](OC(C)=O)OC(C)=O.O>C1COCC1>[Zn+2:34].[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]([O-:33])=[O:32])[C:3]=12.[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]([O-:33])=[O:32])[C:3]=12

Participants

Conditions

Temperature: 60 °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] was dissolved in THF [0.5 mL] and heated to 60° C. Aqueous Zn(OAc)2 [8.0 uL, 1.95 M] was added and the reaction mixture was cooled to 35° C. over 24 h. Water [8 uL] was added and the mixture was stirred at room temperature for 24 h. The reaction mixture was concentrated to dryness and EtOAc was added to provide a white solid which was collected by filtration.

Workup

temperaturethe reaction mixture was cooled to 35° C. over 24 h
concentrationThe reaction mixture was concentrated to dryness and EtOAc
additionwas added
customto provide a white solid which
filtrationwas collected by filtration

Sources & evidence

ORD record: ord-b365c1797b344cbfacf576fe8c24f9b9
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085581B2

Reaction notes

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