Potassium Carbonate → {(R)-1-[6-[2,2-Bis-(4-hydroxy-phenyl)-ethylamino]-9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-9H-purin-2-yl]-pyrrolidin-3-yl}-carbamic acid phenyl ester

HRID 2382417Notes

Reaction equation

HRID 2382417 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:15]=[C:14]3[C:10]([N:11]=[CH:12][N:13]3[C@@H:16]3[CH2:20][C@H:19]([NH:21][C:22](=[O:25])[CH2:23][CH3:24])[C@@H:18]([OH:26])[C@H:17]3[OH:27])=[C:9]([NH:28][CH2:29][CH:30]([C:38]3[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=3)[C:31]3[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=3)[N:8]=2)[CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[C:51]1([O:57][C:58](Cl)=[O:59])[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>CN1C(=O)CCC1>[C:51]1([O:57][C:58](=[O:59])[NH:1][C@@H:2]2[CH2:6][CH2:5][N:4]([C:7]3[N:15]=[C:14]4[C:10]([N:11]=[CH:12][N:13]4[C@@H:16]4[CH2:20][C@H:19]([NH:21][C:22](=[O:25])[CH2:23][CH3:24])[C@@H:18]([OH:26])[C@H:17]4[OH:27])=[C:9]([NH:28][CH2:29][CH:30]([C:31]4[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=4)[C:38]4[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=4)[N:8]=3)[CH2:3]2)[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 66630815N-((1S,2R,3S,4R)-4-{2-((R)-3-Amino-pyrrolidin-1-yl)-6-[2,2-bis-(4-hydroxy-phenyl)-ethylamino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide

Product 1

HCID 66629707{(R)-1-[6-[2,2-Bis-(4-hydroxy-phenyl)-ethylamino]-9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-9H-purin-2-yl]-pyrrolidin-3-yl}-carbamic acid phenyl ester

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture comprising N-((1S,2R,3S,4R)-4-{2-((R)-3-amino-pyrrolidin-1-yl)-6-[2,2-bis-(4-hydroxy-phenyl)-ethylamino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide (Example 22 step 4) (50 mg, 83 μmol) and potassium carbonate (46 mg, 332 μmol) in NMP (1 ml) is treated with phenylchloroformate and stirred at room temperature for 90 minutes. This mixture was used in the next step without purification.

Workup

  1. customThis mixture was used in the next step without purification

Sources & evidence

ORD record
ord-f23dc241dfc74f8eb30b4c195fc0c1db
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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