Ethyl 2-oxo-2-(10-(trifluoromethylsulfonyloxy)phenanthren-9-yl)acetate → (S)-ethyl 2-tert-butoxy-2-(10 (trifluoromethylsulfonyloxy)phenanthren-9-yl)acetate

HRID 926194Notes

Reaction equation

HRID 926194 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])=[C:7]([C@H:20]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:6]([CH3:31])=[CH:5]2.O=[C:33]([C:39]1C2C(C3C=CC=CC=3C=1OS(C(F)(F)F)(=O)=O)=CC=CC=2)[C:34](OCC)=O>>[C:27]([O:26][C@@H:20]([C:7]1[C:6]2[C:5]([C:4]3[CH:3]=[CH:2][CH:11]=[CH:10][C:9]=3[C:8]=1[O:12][S:13]([C:16]([F:17])([F:18])[F:19])(=[O:14])=[O:15])=[CH:39][CH:33]=[CH:34][CH:31]=2)[C:21]([O:23][CH2:24][CH3:25])=[O:22])([CH3:29])([CH3:28])[CH3:30]

Participants

3

Reactant 2

HCID 89676702Ethyl 2-oxo-2-(10-(trifluoromethylsulfonyloxy)phenanthren-9-yl)acetateHCID 89681724(S)-ethyl 2-(6-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate

Product 1

HCID 89681786(S)-ethyl 2-tert-butoxy-2-(10 (trifluoromethylsulfonyloxy)phenanthren-9-yl)acetate

Procedure

Prepared by the similar method to make (S)-ethyl 2-(6-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate in Example 20, using ethyl 2-oxo-2-(10-(trifluoromethylsulfonyloxy)phenanthren-9-yl)acetate instead of ethyl 2-(6-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate. 1H-NMR: 400 MHz, (CDCl3) δ: 8.74-8.69 (m, 2H), 8.41 (d, J=4.4 Hz, 1H), 8.19 (d, J=4.2 Hz, 1H), 7.79-7.61 (m, 4H), 6.00 (s, 1H), 4.189-4.14 (m, 1H), 4.05-4.00 (m, 1H), 1.25 (s, 9H), 1.03 (t, J=7 Hz, 3H).

Workup

  1. customPrepared by the similar method

Sources & evidence

ORD record
ord-b8c851df60e94d308fedcf912ed645e2
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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