((1R)-2,2-difluorocyclopropyl)methyl 4-nitrobenzenesulfonate → tert-butyl ((2S)-4-(2-(4-(((1R)-2,2-difluorocyclopropyl)methoxy)phenyl)[1,3]oxazolo[5,4-d]pyrimidin-5-yl)butan-2-yl)carbamate

HRID 2277336Notes

Reaction equation

HRID 2277336 reaction equation
C(O[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[N:18]=[C:19]([C:24]#[C:25][C@@H:26]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH3:27])[N:20]=[CH:21][C:22]=3[N:23]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[N+](C1C=CC(S([O:48][CH2:49][C@H:50]2[CH2:52][C:51]2([F:54])[F:53])(=O)=O)=CC=1)([O-])=O>>[F:54][C:51]1([F:53])[CH2:52][C@@H:50]1[CH2:49][O:48][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[O:16][C:17]3[N:18]=[C:19]([CH2:24][CH2:25][C@@H:26]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH3:27])[N:20]=[CH:21][C:22]=3[N:23]=2)=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 86731320((1R)-2,2-difluorocyclopropyl)methyl 4-nitrobenzenesulfonateHCID 86731426HCID 86731426, compound

Product 1

HCID 86731427tert-butyl ((2S)-4-(2-(4-(((1R)-2,2-difluorocyclopropyl)methoxy)phenyl)[1,3]oxazolo[5,4-d]pyrimidin-5-yl)butan-2-yl)carbamate

Procedure

Using tert-butyl ((2S)-4-(2-(4-(benzyloxy)phenyl) [1,3]oxazolo[5,4-d]pyrimidin-5-yl)but-3-yn-2-yl)carbamate and ((1R)-2,2-difluorocyclopropyl)methyl 4-nitrobenzenesulfonate, and in the same manner as in Step A of Example 4 and Example 5, the title compound was obtained.

Sources & evidence

ORD record
ord-4c510a071cfd47ac8a069347eb19fa3d
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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