(1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-1-(methylcarbamoyloxy)cyclopenta[c]-pyrane-4-carboxylic acid dimethylamide → (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy) cyclopenta [c]-pyrane-4-carboxylic acid

HRID 1976361Notes

Reaction equation

C[N:2]([CH3:20])[C:3]([C:5]1[C@H:6]2C[C@@H]3O[C@@H]3[C@@H:7]2[C@H:8](OC(=O)NC)OC=1)=[O:4].[CH2:21]([N:23](CC)[C:24]([C:26]1[C@H:27]2[CH2:39][C@@H:38]3[O:40][C@:37]3([CH3:41])[C@@H:28]2[C@H:29]([O:32][C:33](=[O:36])[NH:34][CH3:35])[O:30][CH:31]=1)=[O:25])[CH3:22]>>[N:2]1([NH:23][C:24]([C:26]2[C@H:27]3[CH2:39][C@@H:38]4[O:40][C@:37]4([CH3:41])[C@@H:28]3[C@H:29]([O:32][C:33](=[O:36])[NH:34][CH3:35])[O:30][CH:31]=2)=[O:25])[CH2:3][CH2:5][CH2:6][CH2:20]1.[CH2:21]([NH:23][C:24]([C:26]1[C@H:27]2[CH2:39][C@@H:38]3[O:40][C@:37]3([CH3:41])[C@@H:28]2[C@H:29]([O:32][C:33](=[O:36])[NH:34][CH3:35])[O:30][CH:31]=1)=[O:25])[C:22]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:3]=1.[O:40]1[C@@:37]2([CH3:41])[C@@H:38]1[CH2:39][C@@H:27]1[C:26]([C:24]([OH:25])=[O:4])=[CH:31][O:30][C@@H:29]([O:32][C:33](=[O:36])[NH:34][CH3:35])[C@H:28]12

Participants

Reactant 2

HCID 57301816(1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-1-(methylcarbamoyloxy)cyclopenta[c]-pyrane-4-carboxylic acid dimethylamide

HCID 86756670HCID 86756670, compound

Product 3

HCID 18397301(1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy) cyclopenta [c]-pyrane-4-carboxylic acid

HCID 57159362(1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy) cyclopenta [c]-pyrane-4-carboxylic acid benzylamide

HCID 86755115(1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy)cyclopenta[c]-pyrane-4-carboxylic acid pyrrolidylamide

Procedure

(1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-1-(methylcarbamoyloxy) cyclopenta [c]-pyrane-4-carboxylic acid dimethylamide (Table 4, Compound No. 18), (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy) cyclopenta [c]-pyrane-4-carboxylic acid diethylamide (Table 4, Compound No. 19), (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy) cyclopenta [c]-pyrane-4-carboxylic acid pyrrolidylamide (Table 5, Compound No. 25), and (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy) cyclopenta [c]-pyrane-4-carboxylic acid benzylamide (Table 6, Compound No. 27) were produced in the same manner from (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy) cyclopenta [c]-pyrane-4-carboxylic acid. The physicochemical properties of the above compounds are described in the attached tables (corresponding to Table No. and Compound No.).

Sources & evidence

ORD record: ord-8b07cf4d8ca142caaf87446570169789
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06225478B1

Reaction notes

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