Isopropanol → (7R,7aS)-8-(7-Hydroxy-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)benzo[1,4]dioxane-5-carbonitrile

HRID 751047Notes

Reaction equation

HRID 751047 reaction equation
BrC1[C:7]2[O:8]CC[O:11][C:6]=2C(NC(=O)C)=CC=1.C(C1C2CCCCC=2C(NC(=O)C)=CC=1)#N.[OH:32][C@H:33]1[C@@H:40]2[N:36]([C:37](=[O:54])[N:38]([C:42]3[C:51]4CCCC[C:46]=4[C:45]([C:52]#[N:53])=[CH:44][CH:43]=3)[C:39]2=[O:41])[CH2:35][CH2:34]1.C(O)(C)C>CCCCCC>[OH:32][C@H:33]1[C@@H:40]2[N:36]([C:37](=[O:54])[N:38]([C:42]3[C:51]4[O:8][CH2:7][CH2:6][O:11][C:46]=4[C:45]([C:52]#[N:53])=[CH:44][CH:43]=3)[C:39]2=[O:41])[CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 9904811(7R,7aS)-4-(7-Hydroxy-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carbonitrileHCID 23269228N-(8-Bromobenzo[1,4]dioxan-5-yl)-acetamideHCID 68460315N-(4-Cyano-5,6,7,8-tetrahydronaphthalen-1-yl)-acetamide

Product 1

HCID 59754293(7R,7aS)-8-(7-Hydroxy-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)benzo[1,4]dioxane-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The title compound (32 mg) was prepared from compound 8D and isolated as a white solid by procedures analogous to those described in Example 2 (2C to 2F). mp196-197° C.; HPLC: 99% at 12.31 min (retention time) (CHIRALPAK® OD column 4.6×250 mm; 25% isopropanol in hexane over 30 min, 1 mL/min, UV detection at 220 nm); MS (ES) m/z 322 [M+1]+.

Workup

  1. customisolated as a white solid by procedures analogous to

Sources & evidence

ORD record
ord-2fd20c4c61ed489b903099f942fd1365
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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