(R)-tert-butyl 2,2,4-trimethyl-4-(5-(4-(6-phenylhexyloxy)-3-(trifluoromethyl)phenyl)thiazol-2-yl)oxazolidine-3-carboxylate → (S)-2-Amino-2-(5-(4-(6-phenylhexyloxy)-3-(trifluoromethyl)phenyl)thiazol-2-yl)propan-1-ol

HRID 2357086Notes

Reaction equation

HRID 2357086 reaction equation
CC1(C)[N:6](C(OC(C)(C)C)=O)[C@@:5]([CH3:42])([C:14]2[S:15][C:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[C:21]([C:38]([F:41])([F:40])[F:39])[CH:20]=3)=[CH:17][N:18]=2)[CH2:4][O:3]1>C(#N)C.O>[NH2:6][C@@:5]([C:14]1[S:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[C:21]([C:38]([F:40])([F:41])[F:39])[CH:20]=2)=[CH:17][N:18]=1)([CH3:42])[CH2:4][OH:3]

Participants

3

Reactant 1

HCID 59384324(R)-tert-butyl 2,2,4-trimethyl-4-(5-(4-(6-phenylhexyloxy)-3-(trifluoromethyl)phenyl)thiazol-2-yl)oxazolidine-3-carboxylate

Product 1

HCID 59384400(S)-2-Amino-2-(5-(4-(6-phenylhexyloxy)-3-(trifluoromethyl)phenyl)thiazol-2-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The title compound was prepared from (R)-tert-butyl 2,2,4-trimethyl-4-(5-(4-(6-phenylhexyloxy)-3-(trifluoromethyl)phenyl)thiazol-2-yl)oxazolidine-3-carboxylate. HPLC retention time on a C18 column (30×4.6 mm, 3.5μ) was 2.41 min with gradient 10-95% acetonitrile-H2O (0.1% TFA) in 3.5 min as mobile phase. MS (ESI, M+H+)=479.4; 1H NMR (400 MHz, CDCl3) δ 7.76 (s, 1H), 7.65 (d, 1H, J=2.0 Hz), 7.55 (dd, 1H, J=8.8 Hz, J=2.0 Hz), 7.28-7.23 (m, 2H), 7.18-7.15 (m, 3H), 6.96 (d, 1H, J=9.2 Hz), 4.06-3.99 (m, 4H), 2.62 (t, 2H, J=7.6 Hz), 1.85-1.78 (m, 5H), 1.69-1.62 (m, 2H), 1.56-1.50 (m, 2H), 1.44-1.38 (m, 2H).

Sources & evidence

ORD record
ord-59d852b05c9e4166b7e96e48fab5ce92
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

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