Water → HCID 178458456, compound

HRID 1526425Notes

Reaction equation

HRID 1526425 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:43]([OH:45])=[O:44])[CH2:36][CH2:37][CH2:38][NH:39][C:40](=[NH:42])[NH2:41].O>CC(C)=O>[NH2:34][C@H:35]([C:43]([OH:45])=[O:44])[CH2:36][CH2:37][CH2:38][NH:39][C:40](=[NH:41])[NH2:42].[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

5

Reactant 3

HCID 962WaterHCID 53362086(R)-2-(9-chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acidHCID 178418600HCID 178418600, compound

Product 1

HCID 178458456HCID 178458456, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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 acetone (0.5 mL) and heated to 60° C. Aqueous L-arginine (14 uL, 2.22 M) was added and the reaction mixture was cooled to 35° C. Water (14 uL) was then added and the mixture was stirred 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

  1. temperaturethe reaction mixture was cooled to 35° C
  2. concentrationThe reaction mixture was concentrated to dryness and EtOAc
  3. additionwas added
  4. customto provide a white solid which
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-c8dcb2a74c744c6a9f1c89022db40f1a
Source dataset
uspto-grants-2015_07
Patent number
US09085581B2

Reaction notes

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