Sodium Bicarbonate → HCID 131721998, compound
Reaction equation
[C:1]([C:4]1[C:5]([OH:29])=[C:6]([CH:26]=[CH:27][CH:28]=1)[C:7]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[OH:23])[C:10]=1[OH:25])=[O:8])([OH:3])=[O:2].C([O-])(O)=O.[Na+].ClC1C=C(CC2C=CC=CC=2O)C(O)=C(C=1)CC1C(O)=C(C=CC=1)C(O[CH2:48][C:49]1[CH2:50][S:51][C@@H:52]2[CH:63]([NH:64][C:65](=[O:74])[CH2:66][O:67][C:68]3[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=3)[C:62](=[O:75])[N:53]2[C:54]=1[C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])=O>>[Cl:15][C:13]1[CH:12]=[C:11]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[OH:23])[C:10]([OH:25])=[C:9]([CH:14]=1)[C:7]([C:6]1[C:5]([OH:29])=[C:4]([CH:28]=[CH:27][CH:26]=1)[C:1]([O:3][CH2:48][C:49]1[CH2:50][S:51][C@@H:52]2[CH:63]([NH:64][C:65](=[O:74])[CH2:66][O:67][C:68]3[CH:69]=[CH:70][CH:71]=[CH:72][CH:73]=3)[C:62](=[O:75])[N:53]2[C:54]=1[C:55]([O:57][C:58]([CH3:59])([CH3:60])[CH3:61])=[O:56])=[O:2])=[O:8]Participants
4
Procedure
Compound 18 (7.33 g, 8.99 mmol) was prepared from 16 (5.30 g, 9.99 mmol), 15 (4.13 g, 10.0 mmol), and NaHCO3 (2.52 g, 30.0 mmol) in 90% yield by the same method used for the preparation of 17. For 18: mp 138-140° C.; 1H NMR (DMSO-d6) d 1.50 (s, 9 H, 3×CH3), 3.72, 3.83 (AB, Jgem=19 Hz, 2 H, CH2S), 4.60 (s, 2 H, OCH2CO), 4.99, 5.29 (AB, Jgem=15 Hz, 2 H, CH2O), 5.18 (d, J=5.0 Hz, 1 H, HC(6)), 5.79 (dd, J=5.0 and 9.5 Hz, 1 H, HC(7)), 6.20 (br, 3 H, 3×OH), 6.90-7.50 (m, 14 H, 4×ArH), 8.30 (d, J=9.5 Hz, 1H, NH); IR (nujol): 3290-3370 (OH, NH), 1792 (β-lactam), 1750 (ester), 1730 (ester), 1688 (amide), 1620 (C═O) cm−1. Anal. (C41H35N2 O12SCI) C, H, N, S, Cl.
Sources & evidence
- ORD record
- ord-e6418e2f2a7643f395f157ac1adf48e2
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06288265B1
Reaction notes
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