Trifluoroacetic acid → (1R,2R,4R)-2-[[[(1R)-1-(Ethoxycarbonyl)-2-vinylcyclopropyl]amino]carbonyl]-4-[(2-[2-(isopropylamino)-1,3-thiazol-4-yl]-7-methoxyquinolin-4-yl]oxy]cyclopentanecarboxylic acid

HRID 643840Notes

Reaction equation

HRID 643840 reaction equation
[CH2:1]([O:3][C:4]([C@@:6]1([NH:11][C:12]([C@@H:14]2[CH2:18][C@@H:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[N:33]=[C:34]([NH:37][CH:38]([CH3:40])[CH3:39])[S:35][CH:36]=4)[CH:21]=3)[CH2:16][C@H:15]2[C:41]([O:43]C(C)(C)C)=[O:42])=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].C(O)(C(F)(F)F)=O.[SiH](CC)(CC)CC>C(Cl)Cl>[CH2:1]([O:3][C:4]([C@@:6]1([NH:11][C:12]([C@@H:14]2[CH2:18][C@@H:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[N:33]=[C:34]([NH:37][CH:38]([CH3:40])[CH3:39])[S:35][CH:36]=4)[CH:21]=3)[CH2:16][C@H:15]2[C:41]([OH:43])=[O:42])=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86614779HCID 86614779, compound

Product 1

HCID 86614778(1R,2R,4R)-2-[[[(1R)-1-(Ethoxycarbonyl)-2-vinylcyclopropyl]amino]carbonyl]-4-[(2-[2-(isopropylamino)-1,3-thiazol-4-yl]-7-methoxyquinolin-4-yl]oxy]cyclopentanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 40 (20 mg, 30 umol) in CH2Cl2 (2 mL) was added TFA (2 mL) and Et3SiH (10 μL, 63 umol). After 2 h the volatiles were evaporated and the product was used without any purification. Title compound: 18 mg, quant. as a white solid.

Workup

  1. customAfter 2 h the volatiles were evaporated
  2. customthe product was used without any purification

Sources & evidence

ORD record
ord-ad6d078398bf4edaa37599dde515368a
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

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