Ethylenediamine → {(1S,2R,3S,4R)-4-[2-(2-Amino-ethylcarbamoyl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-carbamic acid tert-butyl ester

HRID 1882559Notes

Reaction equation

HRID 1882559 reaction equation
C[O:2][C:3]([C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[C@@H:14]2[CH2:18][C@H:17]([N:19]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])C(=O)CC)[C@@H:16]([OH:31])[C@H:15]2[OH:32])=[C:7]([NH:33][CH2:34][CH:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:6]=1)=O.[CH2:48]([NH2:51])[CH2:49][NH2:50]>>[C:27]([O:26][C:24](=[O:25])[NH:19][C@H:17]1[CH2:18][C@@H:14]([N:11]2[CH:10]=[N:9][C:8]3[C:12]2=[N:13][C:5]([C:3](=[O:2])[NH:50][CH2:49][CH2:48][NH2:51])=[N:6][C:7]=3[NH:33][CH2:34][CH:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C@H:15]([OH:32])[C@@H:16]1[OH:31])([CH3:28])([CH3:30])[CH3:29]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 666300679-[(1R,2S,3R,4S)-4-(tert-butoxy-carbonyl-propionyl-amino)-2,3-dihydroxy-cyclopentyl]-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carboxylic acid methyl ester

Product 1

HCID 66630888{(1S,2R,3S,4R)-4-[2-(2-Amino-ethylcarbamoyl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-carbamic acid tert-butyl ester

Conditions

Temperature
90 °C

Procedure

A solution comprising 9-[(1R,2S,3R,4S)-4-(tert-butoxycarbonyl-propionyl-amino)-2,3-dihydroxy-cyclopentyl]-6-(2,2-diphenyl-ethylamino)-9H-purine-2-carboxylic acid methyl ester (3.00 g, 4.66 mmol) in ethylenediamine (5 ml, 75 mmol) is heated at 90° C. for 1 hour. After cooling to room temperature, the ethylenediamine is removed in vacuo and purification by C-18 reverse phase column chromatography eluting with water (100%) followed by MeOH (100%) yields the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe ethylenediamine is removed in vacuo and purification by C-18 reverse phase column chromatography
  3. washeluting with water (100%)

Sources & evidence

ORD record
ord-e2a9e483d2084e66b85f0b7b5013d987
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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