Methanol → HCID 66629967, compound

HRID 1882638Notes

Reaction equation

HRID 1882638 reaction equation
[NH2:1][C@H:2]1[CH2:6][C@@H:5]([N:7]2[CH:15]=[N:14][C:13]3[C:8]2=[N:9][C:10]([N:31]2[CH2:35][CH2:34][C@@H:33]([NH:36][C:37]([NH:39][C:40]4[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=4)=[O:38])[CH2:32]2)=[N:11][C:12]=3[NH:16][CH2:17][CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:4]([OH:46])[C@@H:3]1[OH:47].C([O:51][C@@H:52]([CH3:56])[C:53](Cl)=[O:54])(=O)C.C([O-])([O-])=O.[Na+].[Na+].CO>C1COCC1.CC#N>[C:25]1([CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][NH:16][C:12]2[N:11]=[C:10]([N:31]3[CH2:35][CH2:34][C@@H:33]([NH:36][C:37]([NH:39][C:40]4[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=4)=[O:38])[CH2:32]3)[N:9]=[C:8]3[C:13]=2[N:14]=[CH:15][N:7]3[C@@H:5]2[CH2:6][C@H:2]([NH:1][C:53](=[O:54])[C@@H:52]([OH:51])[CH3:56])[C@@H:3]([OH:47])[C@H:4]2[OH:46])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 11094804(1S)-2-Chloro-1-methyl-2-oxoethyl acetateHCID 666296911-{(R)-1-[9-((1R,2S,3R,4S)-4-amino-2,3-dihydroxy-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-3-pyridin-3-yl-urea

Product 1

HCID 66629967HCID 66629967, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture comprising 1-{(R)-1-[9-((1R,2S,3R,4S)-4-amino-2,3-dihydroxy-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-3-pyridin-3-yl-urea (Example 26 step 2) (0.1 g, 0.16 mmol) and TEA (24 μA, 0.18 mmol) in THF (7 ml) at room temperature is treated with (S)-(−)-2-acetoxy-propionyl chloride (24 mg, 0.16 mmol) in MeCN (1 ml) at (0° C.) over 1 minute. The mixture is allowed to stir at room temperature for 18 h and then treated with sat. Na2CO3 (1 ml) and MeOH (1 ml) and then stirred for a further 2 days. The solvent is removed in vacuo and purification by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water −0.3% NH3) affords the title compound as a white solid. (MH+ 707.7)

Workup

  1. stirringstirred for a further 2 days
  2. customThe solvent is removed in vacuo and purification by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water −0.3% NH3)

Sources & evidence

ORD record
ord-21b88a9382a044fa8493196bbae93ba5
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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