2-Thiophenethiol → HCID 22858277, compound

HRID 375162Notes

Reaction equation

HRID 375162 reaction equation
Cl.N[C@H](C)CSC1SC=CC=1.SC1SC=CC=1.C([O:21][C@@H:22]1[C@H:26]([O:27]C(=O)C)[C@@H:25]([CH2:31][O:32]C(=O)C)[O:24][C@H:23]1[N:36]1[C:54]2[N:53]=[C:52]([Cl:55])[N:51]=[C:40]([NH:41][C@H:42]([CH3:50])[CH2:43][S:44][C:45]3[S:46][CH:47]=[CH:48][CH:49]=3)[C:39]=2[N:38]=[CH:37]1)(=O)C.C[O-].[Na+]>CO>[Cl:55][C:52]1[N:51]=[C:40]([NH:41][C@H:42]([CH3:50])[CH2:43][S:44][C:45]2[S:46][CH:47]=[CH:48][CH:49]=2)[C:39]2[N:38]=[CH:37][N:36]([C:54]=2[N:53]=1)[C@@H:23]1[O:24][C@H:25]([CH2:31][OH:32])[C@@H:26]([OH:27])[C@H:22]1[OH:21]

Participants

6

Reactant 4

HCID 5226742-ThiophenethiolHCID 10942334Sodium MethoxideHCID 22858302HCID 22858302, compoundHCID 67771709HCID 67771709, compound

Product 1

HCID 22858277HCID 22858277, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared according to method A as described in Example 1 by reacting 2-[(R)-2-amino-1-propylthio]thiophene hydrochloride [prepared by a Mitsunobu reaction as described in Example 1 using 2-[(R)-N-tert-butyloxycarbonyl]amino-1-propanol (7.53 g, 43 mmol) and 2-mercaptothiophene (5.00 g, 43 mmol) followed by acidic hydrolysis] (0.63 g, 3.0 mmol) with 9-(2,3,5-tri-O-acetyl-B-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.12 g, 2.5 mmol), followed by deacylation of the purified 2',3',5'-tri-O-acetyl-2-chloro-N-[(R)-1-(2-thienyl)thio-2-propyl]adenosine using sodium methoxide in methanol to provide the title 2-chloro-N-[(R)-1-(2-thienyl)thio-2-propyl]adenosine (0.95 g, 82%) as a foam after column chromatography. 1H NMR (DMSO-d6) δ 1.26 (3H, d, --CHCH3), 2.95-3.18 (2H, ABX, --CH2 --S--), 3.55 and 3.61 (2H, ABX, H-5'a and H-5'b), 3.95 (1H, q, H-4), 4.14 (1H, t, H-3'), 4.44 (1H, m, --CHCH3), 4.54 (1H, t, H-2'), 5.84 (1H, d, H-1'), 7.03 (1H, t, Ar-H), 7.23, 7.61 (2H, 2d, Ar-H), 8.38 (1H, d,-NH), 8.42 (1H, s, H-2). HPLC retention time 19.5 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].

Workup

  1. customThe title compound was prepared
  2. customprepared by a Mitsunobu reaction

Sources & evidence

ORD record
ord-7a808f02d0534c36bbc501539fd82fe3
Source dataset
uspto-grants-1996_01
Patent number
US05484774

Reaction notes

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