(5R,9R)-9-(decanoyloxy)-1-(9H-fluoren-9-yl)-3,12-dioxo-2,11-dioxa-7-thia-4-azahenicosane-5-carboxylic acid → (14R,18R)-14-amino-18-(decanoyloxy)-13,21-dioxo-3,6,9,20-tetraoxa-16-thia-12-azatriacontylphosphonic acid
Reaction equation
[C:1]([O:12][C@H:13]([CH2:39][O:40][C:41](=[O:51])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH2:14][S:15][CH2:16][C@@H:17]([C:36]([OH:38])=O)[NH:18]C(=O)OCC1C2C=CC=CC=2C2C1=CC=CC=2)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[NH2:52][CH2:53][CH2:54][O:55][CH2:56][CH2:57][O:58][CH2:59][CH2:60][O:61][CH2:62][CH2:63][P:64](=[O:71])([O:68]CC)[O:65]CC>>[NH2:18][C@@H:17]([CH2:16][S:15][CH2:14][C@H:13]([O:12][C:1](=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:39][O:40][C:41](=[O:51])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[C:36](=[O:38])[NH:52][CH2:53][CH2:54][O:55][CH2:56][CH2:57][O:58][CH2:59][CH2:60][O:61][CH2:62][CH2:63][P:64](=[O:65])([OH:71])[OH:68]Participants
3
Reactant 2
Product 1
Procedure
The title product was prepared from (5R,9R)-9-(decanoyloxy)-1-(9H-fluoren-9-yl)-3,12-dioxo-2,11-dioxa-7-thia-4-azahenicosane-5-carboxylic acid (1 eq) and diethyl 2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethylphosphonate (1.3 eq, from example 18, step 4) by following the procedure described for example 20, step 6-8. 1H NMR (CDCl3): δ 8.67 (br s, 1H), 5.07-5.16 (m, 1H), 3.29 (dd, 1H), 4.08 (dd, 1H), 3.40-3.73 (m, 13H), 3.26-3.38 (m, 2H), 3.02 (dd, 1H), 2.87-2.97 (m, 1H), 2.78 (dd, 1H), 2.68 (dd, 1H), 2.18-2.29 (m, 4H), 1.75-1.89 (m, 2H), 1.46-1.59 (m, 4H), 1.10-1.31 (m, 24H), 0.81 (t, 6H). LRMS [M+H]=743.5.
Sources & evidence
- ORD record
- ord-d7fae221024148c087d7bec59a5ed268
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365506B2
Reaction notes
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