Trifluoroacetic acid → (2S,4R)-4-(4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenoxy)pyrrolidine-2-carboxylic acid

HRID 1177578Notes

Reaction equation

FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:19][C@H:18]([O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[S:28][C:29]4[C:34]([N:35]=3)=[CH:33][CH:32]=[C:31]([C:36]3([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)[CH2:38][CH2:37]3)[N:30]=4)=[CH:23][CH:22]=2)[CH2:17][C@H:16]1[C:45]([OH:47])=[O:46])=O)(C)(C)C>C(Cl)Cl>[C:39]1([C:36]2([C:31]3[N:30]=[C:29]4[S:28][C:27]([C:24]5[CH:25]=[CH:26][C:21]([O:20][C@H:18]6[CH2:19][NH:15][C@H:16]([C:45]([OH:47])=[O:46])[CH2:17]6)=[CH:22][CH:23]=5)=[N:35][C:34]4=[CH:33][CH:32]=3)[CH2:37][CH2:38]2)[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

Conditions

Temperature: 25 °C

Procedure

2,2,2-Trifluoroacetic acid (0.5 mL, 6.49 mmol) was added to a solution of (2S,4R)-1-(tert-butoxycarbonyl)-4-(4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenoxy)pyrrolidine-2-carboxylic acid (130.0 mg, 0.233 mmol) in DCM (4.5 mL) and the resulting solution was stirred at 25° C. for 2 h. The reaction mixture was then concentrated in vacuo, and the residue was taken up in DMSO (2.0 mL) and purified by rpHPLC (10-100% CH3CN/H2O+0.1% TFA) to provide (2S,4R)-4-(4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenoxy)pyrrolidine-2-carboxylic acid as a white solid. MS (ESI) m/z: Calculated: 457.1; Observed: 458.1 (M++1).

Workup

concentrationThe reaction mixture was then concentrated in vacuo
custompurified by rpHPLC (10-100% CH3CN/H2O+0.1% TFA)

Sources & evidence

ORD record: ord-a7498c62da5a40a2a984b90db003b5cc
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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