(5R,9R)-1-(9H-fluoren-9-yl)-3,12-dioxo-9-(tetradecanoyloxy)-2,11-dioxa-7-thia-4-azapentacosane-5-carboxylic acid → (14R, 18R)-14-amino-13,21-dioxo-18-(tetradecanoyloxy)-3,6,9,20-tetraoxa-16-thia-12-azatetratriacontylphosphonic acid

HRID 2407929Notes

Reaction equation

HRID 2407929 reaction equation
C1C2C(COC(=O)[NH:17][C@H:18]([C:56]([OH:58])=O)[CH2:19][S:20][CH2:21][C@H:22]([O:40][C:41](=[O:55])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:23][O:24][C:25](=[O:39])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])C3C(=CC=CC=3)C=2C=CC=1.[NH2:60][CH2:61][CH2:62][O:63][CH2:64][CH2:65][O:66][CH2:67][CH2:68][O:69][CH2:70][CH2:71][P:72](=[O:79])([O:76]CC)[O:73]CC>>[NH2:17][C@@H:18]([CH2:19][S:20][CH2:21][C@H:22]([O:40][C:41](=[O:55])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:23][O:24][C:25](=[O:39])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:56](=[O:58])[NH:60][CH2:61][CH2:62][O:63][CH2:64][CH2:65][O:66][CH2:67][CH2:68][O:69][CH2:70][CH2:71][P:72](=[O:73])([OH:79])[OH:76]

Participants

3

Reactant 2

HCID 10440543(5R,9R)-1-(9H-fluoren-9-yl)-3,12-dioxo-9-(tetradecanoyloxy)-2,11-dioxa-7-thia-4-azapentacosane-5-carboxylic acidHCID 86667767Diethyl 2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethylphosphonate

Product 1

HCID 53476663(14R, 18R)-14-amino-13,21-dioxo-18-(tetradecanoyloxy)-3,6,9,20-tetraoxa-16-thia-12-azatetratriacontylphosphonic acid

Procedure

The title product was prepared from (5R,9R)-1-(9H-fluoren-9-yl)-3,12-dioxo-9-(tetradecanoyloxy)-2,11-dioxa-7-thia-4-azapentacosane-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 7.30 (br s, 1H), 5.13-5.23 (m, 2H), 4.30-4.43 (m, 2H), 4.07-4.20 (m, 2H), 3.44-3.87 (m, 11H), 2.92-3.13 (m, 3H), 2.68-2.92 (m, 4H), 2.22-2.38 (m, 4H), 1.69-2.17 (m, 8H), 1.52-1.67 (m, 4H), 1.10-1.36 (m, 32H), 0.88 (t, 6H). LRMS [M+H]=855.6.

Sources & evidence

ORD record
ord-06731c994eeb4cf497722158a161f485
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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