Hydrochloric Acid → N-{(1S,2R,3S,4R)-4-[2-((R)-3-Amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide dihydrochloride

HRID 215876Notes

Reaction equation

HRID 215876 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[N:21]=[C:20]3[C:16]([N:17]=[CH:18][N:19]3[C@@H:22]3[CH2:26][C@H:25]([NH:27][C:28](=[O:31])[CH2:29][CH3:30])[C@@H:24]([OH:32])[C@H:23]3[OH:33])=[C:15]([NH:34][CH2:35][CH:36]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[N:14]=2)[CH2:9]1)(C)(C)C.[ClH:50]>CO>[ClH:50].[ClH:50].[NH2:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[N:21]=[C:20]3[C:16]([N:17]=[CH:18][N:19]3[C@@H:22]3[CH2:26][C@H:25]([NH:27][C:28](=[O:31])[CH2:29][CH3:30])[C@@H:24]([OH:32])[C@H:23]3[OH:33])=[C:15]([NH:34][CH2:35][CH:36]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[N:14]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66630464{(R)-1-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester

Product 1

HCID 67022955N-{(1S,2R,3S,4R)-4-[2-((R)-3-Amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

{(R)-1-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester (ca 4.80 mmol) is dissolved in 1.25 M HCl in MeOH (60 mL). After stirring at RT for 3 days, the solvent is removed in vacuo to yield the title compound as a brown solid. This is used in the next step without further purification.

Workup

  1. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-5acc51634e3c4fc0a488fcc8b6f1e623
Source dataset
uspto-grants-2012_06
Patent number
US08193164B2

Reaction notes

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