Citric Acid → HCID 9932711, compound

HRID 1379628Notes

Reaction equation

HRID 1379628 reaction equation
[O:1]([CH2:8][CH:9]([NH2:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:15][C@@H:16]1[C@H:20]([O:21]C(=O)C)[C@@H:19]([CH2:25][O:26]C(=O)C)[O:18][C@H:17]1[N:30]1[CH:38]=[N:37][C:36]2[C:31]1=[N:32][C:33]([Cl:40])=[N:34][C:35]=2Cl)(=O)C.C(N(CC)CC)C.[Na].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1.CO.O.C(OCC)(=O)C>[Cl:40][C:33]1[N:34]=[C:35]([NH:11][CH:9]([CH3:10])[CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:36]2[N:37]=[CH:38][N:30]([C:31]=2[N:32]=1)[C@@H:17]1[O:18][C@H:19]([CH2:25][OH:26])[C@@H:20]([OH:21])[C@H:16]1[OH:15]

Participants

10

Reactant 5

HCID 311Citric AcidHCID 8471TriethylamineHCID 370871-Phenoxy-2-propanamineHCID 5360545SodiumHCID 102530272,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine

Product 1

HCID 9932711HCID 9932711, compoundYield 76%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared by reacting 1-phenoxy-2-propylamine (16.62 g, 0.11 mol) with 9-(2,3,5-tri- O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (24.6 g, 55 mmol) in dioxan (250 ml) in the presence of triethylamine (7.23 g, 71.5 mmol) followed by deprotection of the product using a solution of sodium (0.15 g, 6.5 mmol) in methanol (250 ml). The reaction mixture was neutralized with citric acid, and treated with a mixture of ethyl acetate (300 ml) and water (200 ml). The ethyl acetate phase was separated, dried (MgSO4) and evaporated before being purified by flash chromatography on silica gel, eluting initially with dichloromethane, and later with a mixture of dichloromethane and ethanol (9:1). This provided the title 2-chloro- N-(1-phenoxy-2-propyl)adenosine (18.2 g, 76%)(a mixture of diastereoisomers) as an amorphous foam, 1H NMR (DMSO-d6)δ 1.31 (3H, d, --CH3), 3.53-3.59 (1H, m, H-5'a), 3.64-3.71 (1H, m, H-5'b), 3.95 (1H, q, H-4'), 4.06-4.20 (3H, 2 m, H-3' and --CH2 --), 4.54 (1H, m, H-2'), 4.65 (1H, m, --C HCH3), 5.07 (1H, t, 5'-0H), 5.21, 5.50 (2H, 2d, 2'- and 3'--OH), 5.84 (1H, d, H-1'), 6.87-7.00 (3H, m, Ar--H), 7.23-7.32 (2H, t, Ar--H), 8.31-8.45 (2H, m, H-8 and N--H).

Workup

  1. customThe title compound was prepared
  2. customThe ethyl acetate phase was separated
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. custombefore being purified by flash chromatography on silica gel
  6. washeluting initially with dichloromethane
  7. additionlater with a mixture of dichloromethane and ethanol (9:1)

Sources & evidence

ORD record
ord-146315f2e4c34633b5b54314e777fc21
Source dataset
uspto-grants-1997_09
Patent number
US05672588

Reaction notes

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