Triethylamine → (S)-2-Amino-2-(5-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-1,3,4-thiadiazol-2-yl)propyl dihydrogen phosphate

HRID 2357103Notes

Reaction equation

HRID 2357103 reaction equation
[NH2:1][C@@:2]([C:6]1[S:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[C:13]([C:26]([F:29])([F:28])[F:27])[CH:12]=2)=[N:9][N:10]=1)([CH3:5])[CH2:3][OH:4].C([O:32][P:33](Cl)([O:35]CC)=[O:34])C.C(N(CC)CC)C.Br[Si](C)(C)C>C(Cl)Cl>[P:33]([OH:35])([OH:34])([O:4][CH2:3][C@:2]([NH2:1])([C:6]1[S:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[C:13]([C:26]([F:28])([F:27])[F:29])[CH:12]=2)=[N:9][N:10]=1)[CH3:5])=[O:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13139Diethyl chlorophosphateHCID 76113BromotrimethylsilaneHCID 250604211,3,4-Thiadiazole-2-ethanol, beta-amino-beta-methyl-5-[4-(octyloxy)-3-(trifluoromethyl)phenyl]-, (betaS)-

Product 1

HCID 59384310(S)-2-Amino-2-(5-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-1,3,4-thiadiazol-2-yl)propyl dihydrogen phosphateYield 5.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Crude product from E3 (30 mg, 0.069 mmol) was added to diethylchlorophosphate (100 μL, 0.69 mmol) and triethylamine (194 μL, 1.39 mmol,) in DCM and stirred for approx 36 hrs. The reaction mixture was then condensed and treated with bromotrimethylsilan (0.3 mL) in DCM (5 mL) to provide the title compound (˜2 mg). MS (ESI): 511.98 (MH+),

Workup

  1. customcondensed

Sources & evidence

ORD record
ord-e1b0eed9969d45209b1534b3feef85b2
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

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