Triphenylphosphine → HCID 86622619, compound

HRID 1696977Notes

Reaction equation

HRID 1696977 reaction equation
C(OC(=O)O[C@H:6]1[CH2:10][C@@H:9]([N:11]2[CH:19]=[N:18][C:17]3[C:12]2=[N:13][C:14]([Cl:38])=[N:15][C:16]=3[NH:20][CH:21]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[CH:8]=[CH:7]1)C.[NH:40]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([CH:21]([NH:20][C:16]2[N:15]=[C:14]([Cl:38])[N:13]=[C:12]3[C:17]=2[N:18]=[CH:19][N:11]3[C@@H:9]2[CH2:10][C@H:6]([N:40]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C:48]([O:50][C:51]([CH3:52])([CH3:53])[CH3:54])=[O:49])[CH:7]=[CH:8]2)[C:30]2[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 279800Di-tert-butyl IminodicarboxylateHCID 86622620HCID 86622620, compound

Product 1

HCID 86622619HCID 86622619, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Carbonic acid (1S,4R)-4-(6-{[bis-(4-methoxy-phenyl)-methyl]-amino}-2-chloro-purin-9-yl)-cyclopent-2-enyl ester ethyl ester (2.00 g, 3.64 mmol), di-t-butyl iminodicarboxylate (0.87 g, 4.00 mmol) and triphenylphosphine (0.14 g, 0.55 mmol) are placed in an oven-dried flask under an atmosphere of argon. Dry deoxygenated THF (20 ml) is added followed by tetrakis(triphenylphosphine)palladium(0) (0.21 g, 0.18 mmol) and the mixture is stirred at room temperature. The reaction is shown to be complete by LCMS after 3 hours. The solvent is removed in vacuo and the title compound is obtained after purification by flash column chromatography (silica, iso-hexane/ethyl acetate 4:1). 1H nmr (CDCl3, 400 MHz); 8.20(s, 1H), 7.25(d, 4H), 6.85(d, 4H), 6.60(m, 1H), 6.35(m, 1H), 6.10(m, 1H), 5.80(m, 1H), 5.65(m, 1H), 5.35(m, 1H), 3.80(s, 6H), 3.15(m, 1H), 2.10(m, 1H), 1.55(s, 18H).

Workup

  1. customDry
  2. customdeoxygenated THF (20 ml)
  3. additionis added
  4. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-3f440a876ed84c8eb2f6649297ede20e
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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