Bromotrimethylsilane → HCID 53476318, compound

HRID 2204993Notes

Reaction equation

HRID 2204993 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-ad81b3321fb042aca6919c3bd049765b
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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