Hydrochloric Acid → Hydrochloric Acid

HRID 2382446Notes

Reaction equation

HRID 2382446 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].O=C1CCC(=O)N1[O:55][C:56](=O)[CH2:57][NH:58]C(OC(C)(C)C)=O.[ClH:67]>C1COCC1.CCO>[ClH:67].[ClH:67].[NH2:58][CH2:57][C:56]([NH: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:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@H:4]([OH:46])[C@@H:3]1[OH:47])=[O:55]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 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 2

HCID 313Hydrochloric AcidHCID 666312162-Amino-N-((1S,2R,3S,4R)-4-{6-(2,2-diphenyl-ethylamino)-2-[(R)-3-(3-pyridin-3-yl-ureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-acetamide hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 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) (17 mg, 26 μmol) in THF (1 ml) is treated with tert-butoxycarbonylamino-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester (9 mg, 29 μmol) and stirred at room temperature overnight. The resulting solution is treated with 1.25 M HCl in EtOH (1 ml) and stirred at room temperature for 2 days. Purification by C-18 reverse phase column chromatography eluting with acetonitrile:water:HCl (0.1%) (gradient of 0 to 100% acetonitrile) yields the title compound. (MH+ 691.99)

Workup

  1. stirringstirred at room temperature for 2 days
  2. customPurification by C-18 reverse phase column chromatography
  3. washeluting with acetonitrile

Sources & evidence

ORD record
ord-56d7a7a30c7c407ab61c6e2574c6927a
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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