Lawesson's reagent → HCID 86670905, compound
Reaction equation
[C:1](=[N:14][C:15]1[CH:16]=[CH:17][C:18]([F:32])=[C:19]([C@:21]2([CH3:31])[CH2:27][C:26]([CH3:29])([CH3:28])[O:25][CH2:24][C:23](=O)[NH:22]2)[CH:20]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:42]2)=CC=1>O1CCOCC1>[C:1](=[N:14][C:15]1[CH:16]=[CH:17][C:18]([F:32])=[C:19]([C@:21]2([CH3:31])[CH2:27][C:26]([CH3:29])([CH3:28])[O:25][CH2:24][C:23](=[S:42])[NH:22]2)[CH:20]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of (S)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5,7,7-trimethyl-[1,4]oxazepan-3-one (intermediate A17A) (1.15 g, 2.7 mmol) in dioxane (80 ml) at 23° C. was added 2,4-bis-(4-methoxy-phenyl)-[1,3,2,4]dithiadiphosphetane 2,4-disulfide (Lawesson's reagent) (681 mg, 1.7 mmol) and the mixture was stirred at 80° C. for 2 h to obtain a crude solution of the (S)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5,7,7-trimethyl-[1,4]oxazepane-3-thione (intermediate A18A), which was cooled to 23° C. and 1 M HCl (3.4 ml, 3.4 mmol) was added. After 30 min of stirring, the reaction mixture was poured on sat. NaHCO3-solution and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated to give a dark green oil, which was purified by silica gel column chromatography with dichloromethane/ethyl acetate to give the (S)-5-(5-amino-2-fluoro-phenyl)-5,7,7-trimethyl-[1,4]oxazepane-3-thione (575 mg, 76%) as a light brown foam. MS (ISP): m/z=283.1 [(M+H)+].
Sources & evidence
- ORD record
- ord-24e17be9530b4814b830df3b39e0e39c
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748418B2
Reaction notes
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