Tris(hydroxymethyl)aminomethane → (R)-2-(9-chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid 2-amino-2-hydroxymethyl-propane-1,3-diol

HRID 1526424Notes

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:35]([CH2:40][OH:41])([CH2:38][OH:39])[CH2:36][OH:37]>CCOC(C)=O>[NH2:34][C:35]([CH2:40][OH:41])([CH2:38][OH:39])[CH2:36][OH:37].[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: 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, 0.0311 mmol) was dissolved in EtOAc (0.5 mL) and warmed to 60° C. Aqueous 2-amino-2-hydroxymethyl-propane-1,3-diol (TRIS, 8.0 uL, 4.0 M) was added. The reaction mixture was allowed to cool to room temperature over 24 h and the solids were collected by filtration. The PXRD pattern of the title compound is shown in FIG. 13; and the DSC and TGA are shown in FIG. 14.

Workup

temperatureto cool to room temperature over 24 h
filtrationthe solids were collected by filtration

Sources & evidence

ORD record: ord-20e366e471cd4761b7df0d0c278a3712
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085581B2

Reaction notes

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