Ammonia → HCID 44323683, compound
Reaction equation
CC(C)(OC(N1CCCC(O)C1)=O)C.[NH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH:18]([S:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:17]1.C([O:37][C@@H:38]1[C@H:42]([O:43]C(=O)C2C=CC=CC=2)[C@@H:41]([CH2:52][O:53]C(=O)C2C=CC=CC=2)[O:40][C@H:39]1[N:62]1[CH:70]=[N:69][C:68]2[C:63]1=[N:64][C:65]([Cl:72])=[N:66][C:67]=2Cl)(=O)C1C=CC=CC=1.N>>[C:23]1([S:22][CH:18]2[CH2:19][CH2:20][CH2:21][NH:16][CH2:17]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Cl:72][C:65]1[N:66]=[C:67]([NH:15][N:16]2[CH2:21][CH2:20][CH2:19][CH:18]([S:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:17]2)[C:68]2[N:69]=[CH:70][N:62]([C:63]=2[N:64]=1)[C@@H:39]1[O:40][C@H:41]([CH2:52][OH:53])[C@@H:42]([OH:43])[C@H:38]1[OH:37]Participants
Procedure
3-Phenylthiopiperidine was prepared from 1-(1,1-dimethylethoxycarbonyl)-3-hydroxypiperidine by the method described by Kotsuki et al., Tetrahedron Letters, 1991, 32, 4155-4158; otherwise the synthesis proceeded as described in Example 16. 1-Amino-3-phenylthiopiperidine (0.98 g, 4.0 mmol) was reacted with 9-(2',3',5'tri-O-benzoyl-β-D-ribofuranosyl)2,6-dichloro-9H-purine (2.11 g, 3.3 mmol), followed by debenzoylation of the purified product using methanolic ammonia. This provided the title 2-chloro-N-(3-phenylthio-1-piperidinyl)adenosine (0.89 g, 55%) as a foam, 1H NMR (DMSO-d6) δ 3.52-3.59 (1H, m, H-5'a), 3.63-3.71 (1H, m, H-5'b) 3.95 (1H, q, H-4'), 4.13 (1H, q, H-3'), 4.46-4.54 (1H, q, H-2'), 5.07 (1H, t, 5'-0H), 5.22, 5.49 (2H, 2d, 2'- and 3'-OH), 5.84 (1H, d, H-1'), 7.20-7.50 (5H, 2m, Ar--H), 8.43 (1H, s, H-8), 9.50 (1H, s, N--H).
Sources & evidence
- ORD record
- ord-f990a7d9247c468ba667653b6d847a3e
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05578582
Reaction notes
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