Triethylamine → HCID 59384375, compound

HRID 2357100Notes

Reaction equation

HRID 2357100 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)=[CH:9][N:10]=1)([CH3:5])[CH2:3][OH:4].[P:30](Cl)([O:35]CC)([O:32]CC)=[O:31].C(N(CC)CC)C.Br[Si](C)(C)C>C(Cl)Cl>[P:30]([OH:35])([OH:32])([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:29])[F:27])[CH:12]=2)=[CH:9][N:10]=1)[CH3:5])=[O:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13139Diethyl chlorophosphateHCID 76113BromotrimethylsilaneHCID 25060423HCID 25060423, compound

Product 1

HCID 59384375HCID 59384375, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

E1 (25 mg, 1.0 equiv), DCM (5 mL), diethyl chlorophosphate (85 μL, 10.0 equiv) and triethylamine (165 μL, 20.0 equiv) were stirred overnight. The obtained phospho-diester intermediate was reacted with excess bromotrimethylsilane in DCM for 5 hrs. The resulting phosphate was purified by preparative HPLC as the trifluoroacetate salt (10 mg). MS (ESI, M+H+)=511.1.

Workup

  1. customThe resulting phosphate was purified by preparative HPLC as the trifluoroacetate salt (10 mg)

Sources & evidence

ORD record
ord-cf5d552473344cb7bed4076a30c57554
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

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