phenylalaninol, (S)- → Acetic acid ((1S,2R,3S,4R)-4-{2-chloro-6-[(S)-1-hydroxymethyl-2-(4-hydroxy-phenyl)-ethylamino]-purin-9-yl}-2,3-dihydroxy-cyclopentylcarbamoyl)-methyl ester

HRID 1882544Notes

Reaction equation

HRID 1882544 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([NH:16][C:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])=[O:18])[C@@H:13]([OH:24])[C@H:12]2[OH:25])=[C:4]([NH:26][C@H:27]([CH2:35][OH:36])[CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:3]=1.N[C@@H](CC1C=CC=CC=1)C[OH:40]>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([NH:16][C:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])=[O:18])[C@@H:13]([OH:24])[C@H:12]2[OH:25])=[C:4]([NH:26][C@H:27]([CH2:35][OH:36])[CH2:28][C:29]2[CH:34]=[CH:33][C:32]([OH:40])=[CH:31][CH:30]=2)[N:3]=1

Participants

3

Reactant 2

HCID 447213phenylalaninol, (S)-HCID 86632439Acetic acid {(1S,2R,3S,4R)-4-[2-chloro-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentylcarbamoyl}-methyl ester

Product 1

HCID 86647546Acetic acid ((1S,2R,3S,4R)-4-{2-chloro-6-[(S)-1-hydroxymethyl-2-(4-hydroxy-phenyl)-ethylamino]-purin-9-yl}-2,3-dihydroxy-cyclopentylcarbamoyl)-methyl ester

Procedure

The title compound is prepared analogously to acetic acid {(1S,2R,3S,4R)-4-[2-chloro-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentylcarbamoyl}-methyl ester (intermediate ZM), by substituting 4-((S)-2-amino-3-hydroxy-propyl)-phenol for (S)-2-amino-3-phenyl-propan-1-ol.

Sources & evidence

ORD record
ord-ba0977f4bb4445efa8a82bb9cd68ed6e
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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