Hydrochloric Acid → (1S,2R,3S,5R)-3-Amino-5-{6-[2,2-bis-(4-hydroxy-phenyl)-ethylamino]-2-chloro-purin-9-yl}-cyclopentane-1,2-diol

HRID 2382404Notes

Reaction equation

HRID 2382404 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:49]2[CH:54]=[CH:53][C:52]([OH:55])=[CH:51][CH:50]=2)[CH2:9][NH:10][C:11]2[N:19]=[C:18](N3CC[C@@H](NC(NCC4C=CC=C(O)C=4)=O)C3)[N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][N:15]3[C@@H:37]2[CH2:41][C@H:40]([NH:42]C(=O)CO)[C@@H:39]([OH:47])[C@H:38]2[OH:48])=[CH:4][CH:3]=1.[ClH:56]>CO.O1CCOCC1>[NH2:42][C@H:40]1[CH2:41][C@@H:37]([N:15]2[CH:14]=[N:13][C:12]3[C:16]2=[N:17][C:18]([Cl:56])=[N:19][C:11]=3[NH:10][CH2:9][CH:8]([C:49]2[CH:54]=[CH:53][C:52]([OH:55])=[CH:51][CH:50]=2)[C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)[C@H:38]([OH:48])[C@@H:39]1[OH:47]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 24862964n-[(1s,2r,3s,4r)-4-(6-[2,2-Bis-(4-hydroxy-phenyl)-ethylamino]-2-{(r)-3-[3-(3-hydroxy-benzyl)-ureido]-pyrrolidin-1-yl}-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-2-hydroxy-acetamide

Product 1

HCID 86647548(1S,2R,3S,5R)-3-Amino-5-{6-[2,2-bis-(4-hydroxy-phenyl)-ethylamino]-2-chloro-purin-9-yl}-cyclopentane-1,2-diol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of Example 7 step 1 (3.45 g, 5.80 mmol) in methanol (7 ml) is treated with 4M HCl in dioxane (3 ml) and the reaction mixture is stirred at room temperature overnight. The solvent is removed in vacuo and the residue is partitioned between saturated sodium bicarbonate solution and DCM. The organic portion is separated, dried (MgSO4) and concentrated in vacuo to afford the title compound.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between saturated sodium bicarbonate solution and DCM
  3. customThe organic portion is separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-14dbb417d0fe4b71ad2769c5e0f80918
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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