Trifluoroacetic acid → HCID 131735599, compound

HRID 527737Notes

Reaction equation

HRID 527737 reaction equation
C(OC([N:8]1[C@H:12]([C:13](=[O:25])[NH:14][C@H:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16]2)[CH2:11][Si:10]([CH3:27])([CH3:26])[CH2:9]1)=O)(C)(C)C.[C:28]([OH:34])([C:30]([F:33])([F:32])[F:31])=[O:29]>C(Cl)Cl>[OH:34][C:28]([C:30]([F:33])([F:32])[F:31])=[O:29].[CH3:26][Si:10]1([CH3:27])[CH2:11][C@@H:12]([C:13]([NH:14][C@H:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16]2)=[O:25])[NH:8][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89930823HCID 89930823, compound

Product 1

HCID 131735599HCID 131735599, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl-3,3-dimethyl-5-((R)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamoyl)-1,3-azasilolidine-1-carboxylate (4.9 g, 12 mmol) in CH2Cl2 (50 mL) was added TFA (7 mL) at rt. After 4 h, the reaction mixture was concentrated in vacuo to obtain (R)-3,3-dimethyl-N—((R)-1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-azasilolidine-5-carboxamide TFA salt (5.0 g, 12 mmol, 100% yield) as a white solid, which was used directly in the next step. 1H NMR (400 MHz, CD3OD) δ 7.14-7.25 (m, 4H), 5.12 (t, J=5.5 Hz, 1H), 4.0 (dd, J=11.9, 6.6 Hz, 1H), 2.79 (m, 2H), 2.76 (d, J=4.5 Hz, 1H), 2.45 (dd, J=15, 4.5 Hz, 1H), 1.85-2.06 (m, 4H), 1.53 (dd, J=15, 6.8 Hz, 1H), 1.08 (dd, J=15, 4.5 Hz, 1H), 0.41 (3H), 0.38 (s, 3H); MS(ESI+) m/z 289 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-5cc34c1ed1ed4352856180f8281ba681
Source dataset
uspto-grants-2016_05
Patent number
US09345740B2

Reaction notes

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