2',3',5'-tri-O-benzoyl-2-chloro-N-[(R)-1-(2-thiazolyl)thio-2-propyl]adenosine → Adenosine

HRID 2292595Notes

Reaction equation

HRID 2292595 reaction equation
C([O:9][C@@H:10]1[C@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@H:11]1[N:34]1[C:52]2[N:51]=[C:50](Cl)[N:49]=[C:38]([NH:39][C@H](C)CSC3SC=CN=3)[C:37]=2[N:36]=[CH:35]1)(=O)C1C=CC=CC=1>N>[C@@H:11]1([N:34]2[C:52]3[N:51]=[CH:50][N:49]=[C:38]([NH2:39])[C:37]=3[N:36]=[CH:35]2)[O:12][C@H:13]([CH2:24][OH:25])[C@@H:14]([OH:15])[C@H:10]1[OH:9]

Participants

3

Reactant 1

HCID 228583172',3',5'-tri-O-benzoyl-2-chloro-N-[(R)-1-(2-thiazolyl)thio-2-propyl]adenosine

Product 1

HCID 60961AdenosineYield 79.8%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Conditions

Temperature
20 °C

Procedure

2',3',5'-Tri-O-benzoyl-2-chloro-N-[(R)-1-(2-thiazolyl)thio-2-propyl]adenosine (1.2 g, 1.5 mmol) was dissolved in methanolic ammonia (25 ml) (previously saturated at -10° C.) and stirred at 20° C. for 40 h. The reaction mixture was concentrated to an oil at reduced pressure and purified by flash chromatography eluting with a mixture of dichloromethane, ethanol and ammonia (90:10:1), to provide the title 2-chloro-N-[(R)-1-(2-thiazolyl)thio-2-propyl)]adenosine (0.32 g, 46%) as a foam, 1H NMR (DMSO-d6) δ1.31 (3H, d, CHCH3), 3.95 (1H, q, H-4'), 4.12 (1H, q, H-3'), 4.51 (1H, q, H-2'), 5.07 (1H, t, 5'-OH), 5.22, 5.50 (2H, 2d, 2'-and 3'-OH), 5.82 (1H, d, H-1'), 7.63 (1H, d, Ar--H), 7.72 (1H, d, Ar--H), 8.41 (1H, s, H-8), 8.48 (1H, d, N--H).

Workup

  1. concentrationThe reaction mixture was concentrated to an oil at reduced pressure
  2. custompurified by flash chromatography
  3. washeluting with a mixture of dichloromethane, ethanol and ammonia (90:10:1)

Sources & evidence

ORD record
ord-1dc76612260446b6b5c21297eafec1dd
Source dataset
uspto-grants-1997_11
Patent number
US05683989

Reaction notes

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