Sodium Carbonate → HCID 20665002, compound
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C@@H:14]([O:53][CH:54]1[CH2:59][CH2:58][CH2:57][CH2:56][O:55]1)[CH2:15][N:16]([C:43]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:44])[CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]([NH:25][C:26]([O:28][CH2:29][CH:30]1[C:42]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:36]2[C:31]1=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27])[C:22]([OH:24])=[O:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[C@@H](CCCCN(C(OCC1C=CC=CC=1)=O)C[C@@H](OC1CCCCO1)CCNC(OCC1C=CC=CC=1)=O)C(O)=O.C1C(=O)N(OC(OCC2C3C(=CC=CC=3)C3C2=CC=CC=3)=O)C(=O)C1.C([O-])([O-])=O.[Na+].[Na+]>>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C@H:14]([O:53][CH:54]1[CH2:59][CH2:58][CH2:57][CH2:56][O:55]1)[CH2:15][N:16]([C:43]([O:45][CH2:46][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)=[O:44])[CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]([NH:25][C:26]([O:28][CH2:29][CH:30]1[C:42]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:36]2[C:31]1=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27])[C:22]([OH:24])=[O:23])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
5
Procedure
According to the method described for the preparation of 11a, 18b (26 mg, 44 μmol) was reacted with 9-fluorenylmethyl N-succinimidyl carbonate (22 mg, 66 μmol) and Na2CO3 (9 mg, 88 μmol) to give 11b (20 mg, 55%) as a colorless oil: 1H NMR δ 1.14-1.96 (m, 14H), 3.04-3.55 (m, 6H), 3.64-3.98 (m, 3H), 4.14 (m, 1H), 4.20 (t, 1H, J=6.9), 4.34 (d, 2H, J=6.9), 4.38-4.61 (m, 1H), 5.05 (s, 2H), 5.09 (s, 2H), 7.20-7.42 (m, 14H), 7.65 (m, 2H), 7.78 (d, 2H, J=7.4); HRMS m/z calcd for C46H54N3O10 808.3809, found 808.3839. Anal. calcd. for C46H53N3O10: C68.38, H 6.61, N 5.20. Found: C 68.26, H 6.69, N 5.13.
Sources & evidence
- ORD record
- ord-3d60119b981848c4837438f06858028d
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06248866B1
Reaction notes
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