Tetrahydrofuran → HCID 9917983, compound

HRID 895769Notes

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](O)=[O:22])[C:13]([CH2:24][O:25][C:26]2[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=2)=[C:12]3[C:36]([N:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)=[O:37])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.[NH2:54][C:55]1[CH:56]=[C:57]([CH:62]=[CH:63][CH:64]=1)[C:58]([O:60]C)=[O:59].C1COCC1>CN(C1C=CN=CC=1)C.C(OCC)(=O)C.O>[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:54][C:55]2[CH:56]=[C:57]([CH:62]=[CH:63][CH:64]=2)[C:58]([OH:60])=[O:59])=[O:22])[C:13]([CH2:24][O:25][C:26]2[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=2)=[C:12]3[C:36]([N:38]2[CH2:39][CH2:40][CH2:41][CH2:42]2)=[O:37])=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 25 °C

Procedure

The compound of Example 50 (1 eq) was weighed into a flask and to this was added EDCI (3 eq), DMAP (1.2 eq), methyl 3-aminobenzoate (1.2 eq) followed by anhydrous THF (0.04M) and the reaction mixture was then stirred at 25° C. for 2 d. Worked up with ethyl acetate/water followed by washing the organic layer with 1N HCl, saturated bicarbonate and brine. Recrystallization from ethyl acetate/hexane afforded the desired product in 88% yield.

Workup

washby washing the organic layer with 1N HCl, saturated bicarbonate and brine
customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record: ord-ef0170ece09942aeb4550638bb73db3d
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916841B2

Reaction notes

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