Acetoxyacetyl chloride → Acetic acid {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentylcarbamoyl}-methyl ester

HRID 1929771Notes

Reaction equation

HRID 1929771 reaction equation
Cl.Cl.[NH2:3][C@H:4]1[CH2:8][C@@H:7]([N:9]2[CH:17]=[N:16][C:15]3[C:10]2=[N:11][C:12]([Cl:33])=[N:13][C:14]=3[NH:18][CH2:19][CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:6]([OH:34])[C@@H:5]1[OH:35].[C:36]([O:39][CH2:40][C:41](Cl)=[O:42])(=[O:38])[CH3:37]>C1COCC1>[Cl:33][C:12]1[N:11]=[C:10]2[C:15]([N:16]=[CH:17][N:9]2[C@@H:7]2[CH2:8][C@H:4]([NH:3][C:41]([CH2:40][O:39][C:36](=[O:38])[CH3:37])=[O:42])[C@@H:5]([OH:35])[C@H:6]2[OH:34])=[C:14]([NH:18][CH2:19][CH:20]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:13]=1

Participants

4

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 86637574(1S,2R,3S,5R)-3-amino-5-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol dihydrochloride

Product 1

HCID 86637573Acetic acid {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentylcarbamoyl}-methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of (1S,2R,3S,5R)-3-amino-5-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol dihydrochloride (Intermediate AAI13) (250 mg, 0.46 mmol) in dry THF (10 mL) is treated with TEA (0.188 g, 1.86 mmol) followed by acetoxyacetylchloride (0.064 g, 0.46 mmol) and then stirred at room temperature for 30 minutes. The solvent is removed in vacuo and the solvent is partitioned between DCM and 0.1 M HCl. The organic portion is separated and washed with brine, dried (MgSO4) and concentrated in vacuo to afford the title product. MS (ES+) m/e 565.38 (MH+).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe solvent is partitioned between DCM and 0.1 M HCl
  3. customThe organic portion is separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5fb4b62a53e4ee4a6b19c882b9a055c
Source dataset
uspto-grants-2012_05
Patent number
US08188100B2

Reaction notes

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