Bromotrimethylsilane → HCID 53476318, compound

HRID 2407889Notes

Reaction equation

HRID 2407889 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][CH2:11][O:12][CH2:13][C@H:14]([CH3:53])[NH:15][C:16](=[O:52])[C@@H:17]([NH2:51])[CH2:18][S:19][CH2:20][C@H:21]([O:37][C:38](=[O:50])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:22][O:23][C:24](=[O:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])(=[O:8])[O:5]CC)C.C[Si](Br)(C)C>C(Cl)Cl>[NH2:51][C@@H:17]([CH2:18][S:19][CH2:20][C@H:21]([O:37][C:38](=[O:50])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:22][O:23][C:24](=[O:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:16](=[O:52])[NH:15][C@@H:14]([CH3:53])[CH2:13][O:12][CH2:11][CH2:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86678285HCID 86678285, compound

Product 1

HCID 53476318HCID 53476318, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (6S,9R,13R)-9-amino-13-(dodecanoyloxy)-6-methyl-8,16-dioxo-4,15-dioxa-11-thia-7-azaheptacosylphosphonic acid diethyl ester (1 eq, from the previous step) in DCM (0.1 M) was added TMSBr (10 eq) and stirred at room temperature overnight. The reaction mixture was concentrated en vaccuo. The crude mixture was purified by reverse phase high performance liquid chromatography (HPLC) with C4 column eluting with a gradient of 40-80% MeCN/10 mM NH4OAc (95:5) in 10 mM NH4OAc (pH 9). The fractions containing the product were combined and lyophilized to give the desired product as a solid. 1H NMR (DMSO-d6): δ 7.97 (d, 1H), 5.09 (m, 1H), 4.27 (dd, 1H), 4.09 (dd, 1H), 3.86 (m, 1H), 3.20-3.43 (m, 5H), 2.59-2.85 (m, 4H), 2.24-2.27 (m, 4H), 1.62-1.69 (m, 2H), 1.23-1.51 (m, 38H), 1.14 (d, 3H), 0.83-0.88 (m, 6H). LRMS [M+H]=739.4.

Workup

  1. concentrationThe reaction mixture was concentrated en vaccuo
  2. customThe crude mixture was purified by reverse phase high performance liquid chromatography (HPLC) with C4 column
  3. washeluting with a gradient of 40-80% MeCN/10 mM NH4OAc (95:5) in 10 mM NH4OAc (pH 9)
  4. additionThe fractions containing the product

Sources & evidence

ORD record
ord-f04b5b12fbba45f4b6afc1e3fc6ceaa9
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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