Bromotrimethylsilane → HCID 53476547, compound

HRID 2407913Notes

Reaction equation

HRID 2407913 reaction equation
[NH2:1][C@@H:2]([CH2:20][S:21][CH2:22][C@H:23]([O:39][C:40](=[O:52])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:24][O:25][C:26](=[O:38])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][C:9]([P:12](=[O:19])([O:16]CC)[O:13]CC)([F:11])[F:10])=[O:4].C[Si](Br)(C)C>C(Cl)Cl>[NH2:1][C@@H:2]([CH2:20][S:21][CH2:22][C@H:23]([O:39][C:40](=[O:52])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:24][O:25][C:26](=[O:38])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][C:9]([P:12](=[O:13])([OH:19])[OH:16])([F:11])[F:10])=[O:4]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86678299HCID 86678299, compound

Product 1

HCID 53476547HCID 53476547, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl 4-((R)-2-amino-3-((R)-2,3-bis(dodecanoyloxy)propylthio)propanamido)-1,1-difluorobutylphosphonate (1 eq) in DCM (0.1 M) was added trimethylsilyl bromide (10 eq). The reaction mixture was stirred at room temperature overnight and concentrated. The crude mixture was purified by reverse phase high performance liquid chromatography (HPLC) with C4 column eluting with a gradient of 30-80% MeCN/10 mM NH4OAc (95:5) in 10 mM NH4OAc (pH 9) to give the title compound as a white solid. 1H NMR (CDCl3): δ 8.74 (br s, 1H), 5.07-5.17 (m, 1H), 4.29 (dd, 1H), 4.19 (dd, 1H), 3.66-3.78 (m, 1H), 2.25-3.51 (m, 4H), 2.66-2.98 (m, 4H), 2.23-2.36 (m, 4H), 1.05-1.84 (m, 2H), 1.60-1.84 (m, 2H), 1.44-1.58 (m, 4H), 1.17-1.34 (m, 32H), 0.85 (t, 6H). LRMS [M+H]=731.4.

Workup

  1. concentrationconcentrated
  2. customThe crude mixture was purified by reverse phase high performance liquid chromatography (HPLC) with C4 column
  3. washeluting with a gradient of 30-80% MeCN/10 mM NH4OAc (95:5) in 10 mM NH4OAc (pH 9)

Sources & evidence

ORD record
ord-1e82c50061a34ed7be3e81939e9c0ef0
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

Loading…