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 1882557Notes

Reaction equation

HRID 1882557 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-0cda6c765eee42f688ccb4f2116929b1
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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