(R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((R)-2-dodecanamido-3-(dodecyloxy)propyl)thio)propanoic acid → ((11S,14R,18R)-14-amino-18-dodecanamido-11-methyl-10,13-dioxo-3,6,20-trioxa-16-thia-9,12-diazadotriacontyl)phosphonic acid

HRID 2407940Notes

Reaction equation

C1C2C(COC([NH:18][C@@H:19]([CH2:23][S:24][CH2:25][C@H:26]([NH:41][C:42](=[O:54])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[CH2:27][O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:20]([OH:22])=O)=O)C3C(=CC=CC=3)C=2C=CC=1.[NH2:55][C@@H:56]([CH3:76])[C:57]([NH:59][CH2:60][CH2:61][O:62][CH2:63][CH2:64][O:65][CH2:66][CH2:67][P:68](=[O:75])([O:72]CC)[O:69]CC)=[O:58]>>[NH2:18][C@@H:19]([CH2:23][S:24][CH2:25][C@H:26]([NH:41][C:42](=[O:54])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[CH2:27][O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:20](=[O:22])[NH:55][C@@H:56]([CH3:76])[C:57](=[O:58])[NH:59][CH2:60][CH2:61][O:62][CH2:63][CH2:64][O:65][CH2:66][CH2:67][P:68](=[O:69])([OH:72])[OH:75]

Participants

Reactant 2

HCID 67402076(R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((R)-2-dodecanamido-3-(dodecyloxy)propyl)thio)propanoic acid

HCID 86678315(S)-diethyl (2-(2-(2-(2-aminopropanamido)ethoxy)ethoxy)ethyl)phosphonate

Product 1

HCID 53476781((11S,14R,18R)-14-amino-18-dodecanamido-11-methyl-10,13-dioxo-3,6,20-trioxa-16-thia-9,12-diazadotriacontyl)phosphonic acid

Procedure

The title product was prepared from (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((R)-2-dodecanamido-3-(dodecyloxy)propyl)thio)propanoic acid (1 eq, from example 26, step 8) and (S)-diethyl (2-(2-(2-(2-aminopropoxy)ethoxy)ethoxy)ethyl)phosphonate (1.2 eq, from example 30, step 2) by following the procedure described for example 28, step 3-5. 1H NMR (DMSO-d6): δ 9.38 (br s, 1H), 8.14 (t, 2H), 4.18-4.25 (m, 1H), 3.92-4.00 (m, 1H), 3.06-3.67 (m, 15H), 2.92 (dd, 2H), 2.79 (dd, 2H), 2.59-2.73 (m, 4H), 2.07 (t, 2H), 1.65-1.75 (m, 2H), 1.42-1.50 (m, 4H), 1.21-1.28 (m, 35H), 0.85 (t, 6H). LRMS [M+H]=811.5.

Sources & evidence

ORD record: ord-8b66865005a44661884ad3f4befa2033
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08808703B2

Reaction notes

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