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Triphenylphosphine → HCID 87407705, compound

HRID 1713326
Notes
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Reaction equation

HRID 1713326 reaction equation
[C:1]([Si:5]([CH3:55])([CH3:54])[O:6][C@@H:7]1[C@H:11]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[C@@H:10]([CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[O:9][C@H:8]1[N:29]1[C:38]2[N:37]=[CH:36][N:35]=[C:33]([NH2:34])[C:32]=2[N:31]=[C:30]1[NH:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:43][C:42]=1[OH:53])([CH3:4])([CH3:3])[CH3:2].O[CH2:57][CH2:58][NH:59][C:60](=[O:69])[O:61][CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH2:62]([O:61][C:60]([NH:59][CH2:58][CH2:57][O:53][C:42]1[CH:43]=[C:44]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:45]=[CH:46][C:41]=1[CH2:40][NH:39][C:30]1[N:29]([C:38]2[N:37]=[CH:36][N:35]=[C:33]([NH2:34])[C:32]=2[N:31]=1)[C@@H:8]1[O:9][C@H:10]([CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24])[C@@H:11]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[C@H:7]1[O:6][Si:5]([C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:55])[CH3:54])=[O:69])[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 280458benzyl N-(2-hydroxyethyl)carbamateHCID 67455364HCID 67455364, compound

Product 1

HCID 87407705HCID 87407705, compoundYield 68.4%

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2′,3′,5′-tris-O-(tert-butyldimethyl-silyl)-8-(3-hydroxybiphenyl-4-ylmethylamino)adenosine (0.175 g), benzyl N-(2-hydroxyethyl)carbamate (0.065 g), triphenylphosphine (0.074 g) in tetrahydrofuran (1.1 mL) was stirred at 50° C. for 30 minutes. Diisopropyl azodicarboxylate (40% toluene solution, 0.143 g) was added dropwise, and the resulting mixture was stirred at 50° C. for 24 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/2 to 1/1) to give 8-[3-(2-benzyloxycarbonylaminoethoxy)biphenyl-4-ylmethyl-amino]-2′,3′,5′-tris-O-(tert-butyldimethylsilyl)adenosine (0.146 g). To a solution of 8-[3-(2-benzyloxycarbonyl-aminoethoxy)biphenyl-4-ylmethylamino]-2′,3′,5′-tris-O-(tert-butyldimethylsilyl)adenosine (0.143 g) in methanol (1.5 mL) was added ammonium fluoride (0.323 g), and the resulting mixture was stirred at 60° C. for 13.5 hours. The reaction mixture was cooled to room temperature. Dichloromethane (7.5 mL) was added, and the insoluble material was filtered out. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on aminopropylated silica gel (eluent: dichloromethane/methanol=15/1) to give the title compound (0.077 g).

Workup

  1. stirringthe resulting mixture was stirred at 50° C. for 24 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/2 to 1/1)

Sources & evidence

ORD record
ord-17814d363bd94b49bd68afd66b51ff0f
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07795236B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes