(1S,4R)-4-(2,6-Dichloro-9H-purin-9-yl)cyclopent-2-en-1-ol → [(1S,4R)-4-(2,6-Dichloro-purin-9-yl)-cyclopent-2-enyl]-propionyl-carbamic acid tert-butyl ester

HRID 1696992Notes

Reaction equation

HRID 1696992 reaction equation
C(OC(=O)O[C@H:6]1[CH2:10][C@@H:9]([N:11]2[CH:19]=[N:18][C:17]3[C:12]2=[N:13][C:14]([Cl:21])=[N:15][C:16]=3[Cl:20])[CH:8]=[CH:7]1)C.ClC1N=C2C(N=CN2[C@@H]2C[C@H](O)C=C2)=C(Cl)N=1.[C:40]([O:44][C:45](=[O:51])[NH:46][C:47](=[O:50])[CH2:48][CH3:49])([CH3:43])([CH3:42])[CH3:41].C(N(C(OC(C)(C)C)=O)[C@H]1C[C@@H](N2C=NC3C2=NC(Cl)=NC=3Cl)C=C1)(OC(C)(C)C)=O>>[C:40]([O:44][C:45](=[O:51])[N:46]([C@H:6]1[CH2:10][C@@H:9]([N:11]2[CH:19]=[N:18][C:17]3[C:12]2=[N:13][C:14]([Cl:21])=[N:15][C:16]=3[Cl:20])[CH:8]=[CH:7]1)[C:47](=[O:50])[CH2:48][CH3:49])([CH3:42])([CH3:41])[CH3:43]

Participants

5

Reactant 4

HCID 10378467(1S,4R)-4-(2,6-Dichloro-9H-purin-9-yl)cyclopent-2-en-1-ol2×HCID 14221819Tert-butyl propionylcarbamateHCID 58025018Di-Boc-[(1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl]-amineHCID 58025019Carbonic acid (1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl ester ethyl ester

Product 1

HCID 86622633[(1S,4R)-4-(2,6-Dichloro-purin-9-yl)-cyclopent-2-enyl]-propionyl-carbamic acid tert-butyl ester

Procedure

The title compound is prepared from carbonic acid (1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl ester ethyl ester (an intermediate for preparing the compound of Example 4) and propionyl-carbamic acid tert-butyl ester (see preparation of intermediates) using a procedure analogous to that of di-Boc-[(1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl]-amine (another intermediate for preparing the compound of Example 4). 1H nmr (CDCl3, 400 MHz); 8.70(s, 1H), 6.15(m, 1H), 5.85(m, 1H), 5.80(m, 1H), 5.60(m, 1H), 3.15(m, 1H), 2.75(q, 2H), 2.10(m, 1H), 1.55(s, 9H), 1.15(t, 3H), MS (ES+) m/e 426 (MH+).

Sources & evidence

ORD record
ord-af3bbf95b49e453b8e4197af2f2238ff
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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