Diisopropylamine → HCID 178491472, compound

HRID 2305997Notes

Reaction equation

HRID 2305997 reaction equation
[C:1]1([CH:7]([SiH2:14][CH2:15][CH2:16][P:17]([O:20][C@@H:21]2[C@@H:25]([CH2:26][O:27][C:28]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)([C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=3)[C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[O:24][C@@H:23]([N:51]3[C:68]4[N:67]=[CH:66][N:65]=[C:55]([NH:56][C:57](=[O:64])[C:58]5[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=5)[C:54]=4[N:53]=[CH:52]3)[CH2:22]2)(=O)[OH:18])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:69]([NH:72][CH:73]([CH3:75])[CH3:74])([CH3:71])[CH3:70].BrC1C=C(Br)C=C(Br)C=1OP(OC1C(Br)=CC(Br)=CC=1Br)(OC1C(Br)=CC(Br)=CC=1Br)(Cl)Cl>C(#N)C>[C:1]1([CH:7]([SiH2:14][CH2:15][CH2:16][PH:17]([O:20][C@@H:21]2[C@@H:25]([CH2:26][O:27][C:28]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=3)[O:24][C@@H:23]([N:51]3[C:68]4[N:67]=[CH:66][N:65]=[C:55]([NH:56][C:57](=[O:64])[C:58]5[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=5)[C:54]=4[N:53]=[CH:52]3)[CH2:22]2)([N:72]([CH:73]([CH3:75])[CH3:74])[CH:69]([CH3:71])[CH3:70])[OH:18])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 194959Tris(2,4,6-tribromophenoxy)dichlorophosphoraneHCID 178491473HCID 178491473, compound

Product 1

HCID 178491472HCID 178491472, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 250 mL two necked flask equipped with a magnetic stirrer, a gas inlet for argon, and a septum is assembled under an argon atmosphere. All glassware are dried at 120° C. for 1 hour. The flask is charged with N6-Benzoyl-5′-O-(4,4′dimethoxytrityl)-2′-deoxyadenosine- 3′-O-(2-diphenylmethylsilylethylphosphonate) (0.015 mole) and diisopropylamine (0.12 mole). Anhydrous acetonitrile (200 mL) is added. To this stirred mixture under argon at room temperature is added tris(2,4,6-tribromophenoxy)dichlorophosphorane (0.225 mole). After stirring for three hours, the reaction mixture is filtered, and concentrated under reduced pressure. The crude product is purified by flash chromatography using silica gel to afford the desired product. Triethylamine (1%) is used throughout the purification.

Workup

  1. customAll glassware are dried at 120° C. for 1 hour
  2. filtrationthe reaction mixture is filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product is purified by flash chromatography

Sources & evidence

ORD record
ord-af1a60c5d03e426786a2403991591ff9
Source dataset
uspto-grants-2002_08
Patent number
US06441150B1

Reaction notes

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