(5R,9R)-9-(dodecanoyloxy)-1-(9H-fluoren-9-yl)-3,12-dioxo-2,11-dioxa-7-thia-4-azatricosane-5-carboxylic acid → HCID 53476549, compound

HRID 2407922Notes

Reaction equation

HRID 2407922 reaction equation
[C:1]([O:14][C@H:15]([CH2:41][O:42][C:43](=[O:55])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:16][S:17][CH2:18][C@@H:19]([C:38]([OH:40])=O)[NH:20]C(=O)OCC1C2C=CC=CC=2C2C1=CC=CC=2)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Cl.[NH2:57][CH2:58][CH2:59][O:60][CH2:61][CH2:62][C:63]([P:66](=[O:73])([O:70]CC)[O:67]CC)([F:65])[F:64]>>[NH2:20][C@@H:19]([CH2:18][S:17][CH2:16][C@H:15]([O:14][C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:41][O:42][C:43](=[O:55])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[C:38](=[O:40])[NH:57][CH2:58][CH2:59][O:60][CH2:61][CH2:62][C:63]([P:66](=[O:67])([OH:73])[OH:70])([F:64])[F:65]

Participants

3

Reactant 2

HCID 67414703(5R,9R)-9-(dodecanoyloxy)-1-(9H-fluoren-9-yl)-3,12-dioxo-2,11-dioxa-7-thia-4-azatricosane-5-carboxylic acidHCID 86678306HCID 86678306, compound

Product 1

HCID 53476549HCID 53476549, compound

Procedure

The title product was prepared from (5R,9R)-9-(dodecanoyloxy)-1-(9H-fluoren-9-yl)-3,12-dioxo-2,11-dioxa-7-thia-4-azatricosane-5-carboxylic acid (6, 1 eq) and diethyl 3-(2-aminoethoxy)-1,1-difluoropropylphosphonate hydrochloride (1.2 eq) by following the procedure described for example 19, step 4-6. 1H NMR (CDCl3): δ 8.08 (br s, 1H), 5.11-5.24 (m, 1H), 4.31 (dd, 1H), 4.08-4.25 (m, 2H), 3.64-3.80 (m, 3H), 3.48-3.64 (m, 2H), 2.99-3.19 (m, 3H), 2.82 (dd, 1H), 2.72 (dd, 1H), 2.23-2.37 (m, 6H), 1.51-1.64 (m, 4H), 1.16-1.36 (m, 32H), 0.88 (t, 6H). LRMS [M+H]=761.4.

Sources & evidence

ORD record
ord-dc77e6a443ff481181365e94e7232041
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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