Hydrochloric Acid → HCID 9840375, compound

HRID 1082102Notes

Reaction equation

HRID 1082102 reaction equation
C([O:9][C@@H:10]1[C@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@@H:13]([CH:24]=[CH2:25])[O:12][C@H:11]1[N:26]1[C:37]2[N:36]=[C:35]([Cl:38])[N:34]=[C:30]([NH:31][O:32][CH3:33])[C:29]=2[N:28]=[CH:27]1)(=O)C1C=CC=CC=1.ClC1N=C2C(N=CN2[C@@H]2O[C@H](C(=C)O)[C@@H](OC(=O)C3C=CC=CC=3)[C@H]2OC(=O)C2C=CC=CC=2)=C(Cl)N=1.Cl>N>[Cl:38][C:35]1[N:34]=[C:30]([NH:31][O:32][CH3:33])[C:29]2[N:28]=[CH:27][N:26]([C:37]=2[N:36]=1)[C@@H:11]1[O:12][C@H:13]([CH:24]=[CH2:25])[C@@H:14]([OH:15])[C@H:10]1[OH:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 22868440HCID 22868440, compoundHCID 22868443HCID 22868443, compound

Product 1

HCID 9840375HCID 9840375, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

2',3'-Di-O-benzoyl-2-chloro-5'-deoxy-N-methoxy-5'-methyleneadenosine (0.2 g, 0.4 mmol), prepared by the method described in Example 25 from 2,6-dichloro-9-(2',3'-di-O-benzoyl-5'-methylene-β-D-ribofuranosyl)-9H-purine (0.5 g, 2.0 mmol) and O-methylhydroxlamine hydrochloride (0.167 g, 2.0 mmol), was treated with methanolic ammonia (10 ml) and stirred at ambient temperature for 18 h. The reaction mixture was evaporated and purified by flash chromatography eluting with a mixture of dichloromethane and 10% ammonia in ethanol (19:1) to provide the title 2-chloro-5'-deoxy-N-methoxy-5'-methyleneadenosine (0.03 g, 9%) as a foam, 1H-NMR (400 MHz, DMSO-d6) δ3.79 (3H, s, --CH3), 4.08 (1H, q, H-3'), 4.33 (1H, dt, H-2'), 4.61 (1H, m, H-4'), 5.20 (1H, dd, C=C--H), 5.31 (1H, d, C=C--H), 5.42, 5.59 (2H, 2d, 2'-and 3'-OH), 5.89 (1H, d, H-1'), 6.08 (1H, m, C=C--H), 8.44 (1H, s, H-8), 11.58 (1H, s, N--H). HPLC retention time 7.09 min. (gradient elution over 30 min; 25-45 % acetonitrile/0.1% ammonium sulfate in water), purity 98.6% at 250 nm).

Workup

  1. customThe reaction mixture was evaporated
  2. custompurified by flash chromatography
  3. washeluting with a mixture of dichloromethane and 10% ammonia in ethanol (19:1)

Sources & evidence

ORD record
ord-a9552d5e28f147a3a068f79e0efdb317
Source dataset
uspto-grants-1996_12
Patent number
US05589467

Reaction notes

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