Methanol → HCID 24755621, compound

HRID 1929781Notes

Reaction equation

HRID 1929781 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]([Cl:58])=[N:11][C:12]=3[NH:16][C@@H:17]2[CH2:21][CH2:20][N:19]([C:22]3[N:30]=[C:29]4[C:25]([N:26]=[CH:27][N:28]4[C@@H:31]4[CH2:35][C@H:34]([NH:36][C:37](=[O:40])[CH2:38][CH3:39])[C@@H:33]([OH:41])[C@H:32]4[OH:42])=[C:24]([NH:43][CH2:44][CH:45]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)[C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[N:23]=3)[CH2:18]2)[C@H:4]([OH:59])[C@@H:3]1[OH:60].CO.[C:63](Cl)(=[O:66])[CH2:64][CH3:65]>C1COCC1>[Cl:58][C:10]1[N:9]=[C:8]2[C:13]([N:14]=[CH:15][N:7]2[C@@H:5]2[CH2:6][C@H:2]([NH:1][C:63](=[O:66])[CH2:64][CH3:65])[C@@H:3]([OH:60])[C@H:4]2[OH:59])=[C:12]([NH:16][C@@H:17]2[CH2:21][CH2:20][N:19]([C:22]3[N:30]=[C:29]4[C:25]([N:26]=[CH:27][N:28]4[C@@H:31]4[CH2:35][C@H:34]([NH:36][C:37](=[O:40])[CH2:38][CH3:39])[C@@H:33]([OH:41])[C@H:32]4[OH:42])=[C:24]([NH:43][CH2:44][CH:45]([C:52]4[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=4)[C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[N:23]=3)[CH2:18]2)[N:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 62324Propionyl chlorideHCID 86637577HCID 86637577, compound

Product 1

HCID 24755621HCID 24755621, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-{(1S,2R,3S,4R)-4-[2-{(R)-3-[9-((1R,2S,3R,4S)-4-Amino-2,3-dihydroxy-cyclopentyl)-2-chloro-9H-purin-6-ylamino]-pyrrolidin-1-yl}-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide (32 mg, 0.038 mmol) and TEA (0.016 mL, 0.113 mmol) are suspended in THF (0.5 mL). MeOH (0.5 mL) is added to aid solubility. Propionic acid chloride (0.0035 mL, 0.040 mmol) is added and the reaction mixture is stirred at room temperature overnight. The reaction mixture is reduced in vacuo and purified by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water-0.1% TFA) to yield the title compound (MH+ 894/895).

Workup

  1. custompurified by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water-0.1% TFA)

Sources & evidence

ORD record
ord-2e24f9645c2142ae8d68056248280357
Source dataset
uspto-grants-2012_05
Patent number
US08188100B2

Reaction notes

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