(5R,9R)-1-(9H-fluoren-9-yl)-9-(octanoyloxy)-3,12-dioxo-2,11-dioxa-7-thia-4-azanonadecane-5-carboxylic acid → (14R,18R)-14-amino-18-(octanoyloxy)-13,21-dioxo-3,6,9,20-tetraoxa-16-thia-12-azaoctacosylphosphonic acid
Reaction equation
C1C2C(COC(=O)[NH:17][C@H:18]([C:44]([OH:46])=O)[CH2:19][S:20][CH2:21][C@H:22]([O:34][C:35](=[O:43])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:23][O:24][C:25](=[O:33])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])C3C(=CC=CC=3)C=2C=CC=1.[NH2:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][O:57][CH2:58][CH2:59][P:60](=[O:67])([O:64]CC)[O:61]CC>>[NH2:17][C@@H:18]([CH2:19][S:20][CH2:21][C@H:22]([O:34][C:35](=[O:43])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:23][O:24][C:25](=[O:33])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:44](=[O:46])[NH:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][O:57][CH2:58][CH2:59][P:60](=[O:61])([OH:67])[OH:64]Participants
3
Reactant 2
Product 1
Procedure
The title product was prepared from (5R,9R)-1-(9H-fluoren-9-yl)-9-(octanoyloxy)-3,12-dioxo-2,11-dioxa-7-thia-4-azanonadecane-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 (DMSO-d6): δ 8.18 (t, 1H), 5.04-5.11 (m, 1H), 4.27 (dd, 1H), 4.10 (dd, 1H), 3.46-3.56 (m, 8H), 3.38-3.56 (m, 4H), 3.27-3.36 (m,1H), 3.18-3.25 (m, 2H), 2.74-2.83 (m, 2H), 2.68 (dd, 1H), 2.57 (dd, 1H), 2.21-2.33 (m, 4H), 1.55-1.67 (m, 2H), 1.44-1.55 (m, 4H), 1.16-1.32 (m, 16H), 0.85 (t, 6H). LRMS [M+H]=687.4.
Sources & evidence
- ORD record
- ord-f5922302a3304d8db2902d8799d43bd3
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08808703B2
Reaction notes
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