Trifluoroacetic acid → HCID 89930805, compound

HRID 527748Notes

Reaction equation

HRID 527748 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:34]([N:36]3[C@H:40]([C:41](=[O:53])[NH:42][C@H:43]4[C:52]5[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=5)[CH2:46][CH2:45][CH2:44]4)[CH2:39][Si:38]([CH3:55])([CH3:54])[CH2:37]3)=[O:35])[CH2:20][C:21]3[CH:33]=[CH:32][C:24]([C:25]([O:27]C(C)(C)C)=[O:26])=[CH:23][CH:22]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:34]([N:36]3[C@H:40]([C:41](=[O:53])[NH:42][C@H:43]4[C:52]5[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=5)[CH2:46][CH2:45][CH2:44]4)[CH2:39][Si:38]([CH3:54])([CH3:55])[CH2:37]3)=[O:35])[CH2:20][C:21]3[CH:33]=[CH:32][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=3)=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735600HCID 131735600, compound

Product 1

HCID 89930805HCID 89930805, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((R)-3,3-dimethyl-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,3-azasilolidin-1-yl)-3-oxopropyl)benzoate (0.17 g, 0.22 mmol) in CH2Cl2 (10 mL) was added TFA (1 mL) at rt. After 4 h, the reaction mixture was concentrated in vacuo to obtain the title compound (150 mg, 82% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 12.37 (br. s., 1H), 8.05 (d, J=8.4 Hz, 2H), 7.76 (d, J=7.5 Hz, 2H), 7.56 (dd, J=7.3, 4.4 Hz, 2H), 7.44-7.05 (m, 11H), 6.62-6.52 (m, 2H), 5.23-5.09 (m, 2H), 4.94 (t, J=6.9 Hz, 1H), 4.38-4.11 (m, 3H), 3.33 (d, J=13.2 Hz, 1H), 3.20 (dd, J=14.1, 4.8 Hz, 1H), 3.03-2.93 (m, 2H), 2.86-2.74 (m, 2H), 2.11-2.01 (m, 1H), 1.92-1.79 (m, 3H), 1.27 (d, J=6.6 Hz, 2H), 0.45 (s, 3H), 0.32 (s, 3H); MS(ESI+) m/z 702.1 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-77ff965b272c472ebd09faf79b81eddf
Source dataset
uspto-grants-2016_05
Patent number
US09345740B2

Reaction notes

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