Tetrahydrofuran → HCID 9832360, compound

HRID 895770Notes

Reaction equation

[CH:1]1([C:6]([NH:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH2:18][CH2:19][CH2:20][C:21]([NH:23][C:24]2[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=2)[C:27](O)=[O:28])=[O:22])[C:13]([CH2:33][O:34][C:35]2[CH:44]=[CH:43][C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH:36]=2)=[C:12]3[C:45]([N:47]2[CH2:51][CH2:50][CH2:49][CH2:48]2)=[O:46])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.[F:63][C:64]([F:70])([F:69])[S:65]([NH2:68])(=[O:67])=[O:66].C1COCC1>CN(C1C=CN=CC=1)C.C(OCC)(=O)C.O>[CH:36]1[C:37]2[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:43]=[CH:44][C:35]=1[O:34][CH2:33][C:13]1[N:14]([CH2:18][CH2:19][CH2:20][C:21](=[O:22])[NH:23][C:24]2[CH:32]=[CH:31][CH:30]=[C:26]([C:27]([NH:68][S:65]([C:64]([F:70])([F:69])[F:63])(=[O:67])=[O:66])=[O:28])[CH:25]=2)[C:15]2[C:11]([C:12]=1[C:45]([N:47]1[CH2:48][CH2:49][CH2:50][CH2:51]1)=[O:46])=[CH:10][C:9]([NH:8][C:6]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)=[O:7])=[CH:17][CH:16]=2

Participants

Conditions

Temperature: 25 °C

Procedure

The compound of Example 55 (1 eq) was weighed into a flask and to this was added EDCI (3 eq), DMAP (1.2 eq), trifluoromethanesulfonamide (1.2 eq) followed by anhydrous THF (0.04 M) and the reaction mixture was then stirred at 25° C., overnight. Worked up with ethyl acetate/water followed by washing the organic layer with 1N HCl, saturated bicarbonate and brine. Trituration with CH2Cl2/hexane (8:2) afforded the desired product in 84% yield.

Workup

washby washing the organic layer with 1N HCl, saturated bicarbonate and brine

Sources & evidence

ORD record: ord-d2dcdd49357043d4906961ee1a8c82c9
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916841B2

Reaction notes

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