3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → (S)-tert-butyl 3-(2-chloro-9-methyl-6-(3-methylmorpho-lino)-9H-purin-8-yl)-3-hydroxyazetidine-1-carboxylate

HRID 2063365Notes

Reaction equation

HRID 2063365 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:12]3([OH:18])CCOC[CH2:13]3)[N:8]2[CH3:11])=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]2[CH3:25])[N:3]=1.O=C1C[N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:28]1>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:12]3([OH:18])[CH2:28][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:13]3)[N:8]2[CH3:11])=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]2[CH3:25])[N:3]=1

Participants

3

Reactant 2

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 58222532(S)-4-(2-chloro-9-methyl-6-(3-methylmorpholino)-9H-purin-8-yl)tetrahydro-2H-pyran-4-ol

Product 1

HCID 58222522(S)-tert-butyl 3-(2-chloro-9-methyl-6-(3-methylmorpho-lino)-9H-purin-8-yl)-3-hydroxyazetidine-1-carboxylate

Procedure

This compound (c-1) was prepared in an analogous fashion to (S)-4-(2-chloro-9-methyl-6-(3-methylmorpholino)-9H-purin-8-yl)tetrahydro-2H-pyran-4-ol, using tert-butyl 3-oxoazetidine-1-carboxylate as the starting material. 1H NMR (CDCl3, 400 MHz) δ ppm 5.17 (broad d, 2H), 4.56 (dd, J=16.9, 9.48 Hz, 2H), 4.21 (dd, J=9.48. 2.56 Hz, 1H), 4.04 to 3.96 (m, 1H), 3.82 to 3.71 (m, 5H), 3.59 (td, J=11.6, 2.6 Hz, 1H), 3.47 (broad s, 1H), 2.02 (s, 1H), 1.43 (s, 9H), 1.40 to 1.36 (m, 4H); LC-MS (method A)=439/441 [M+H]+, RT=2.56 min.

Sources & evidence

ORD record
ord-396b9dc15c4845df8db09817dc6deadc
Source dataset
uspto-grants-2012_10
Patent number
US08288381B2

Reaction notes

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