Methanol → HCID 18465905, compound

HRID 2230446Notes

Reaction equation

HRID 2230446 reaction equation
[C:1]([NH:4][CH:5]1[C:11](=[O:12])[N:10]2[CH:13]([C:17]([NH:19][CH:20]([C:29](=[O:42])[CH2:30][O:31][C:32](=[O:41])[C:33]3[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:40])[CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])=[O:18])[CH2:14][CH2:15][CH2:16][N:9]2[C:8](=[O:43])[CH2:7][CH2:6]1)(=[O:3])[CH3:2].CO.[K+].[Br-]>O>[C:1]([NH:4][CH:5]1[C:11](=[O:12])[N:10]2[CH:13]([C:17]([NH:19][CH:20]([C:29](=[O:42])[CH2:30][O:31][C:32](=[O:41])[C:33]3[C:34]([Cl:40])=[CH:35][CH:36]=[CH:37][C:38]=3[Cl:39])[CH2:21][C:22]([OH:24])=[O:23])=[O:18])[CH2:14][CH2:15][CH2:16][N:9]2[C:8](=[O:43])[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 253877Potassium BromideHCID 18465727HCID 18465727, compound

Product 1

HCID 18465905HCID 18465905, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

was synthesized from 216c by the same method as compound 217e as a glassy white solid (166 mg, 66%): mp 85-175° C.; [α]D25 −156 (c 0.13, MeOH; IR (KBr) 3373, 2929, 1742, 1659, 1562, 1533, 1433, 1412, 1274, 1266, 1223, 1197, 1145, 1138, 1H NMR (CD3OD) δ7.38 (3H, s), 5.14-5.03 (1H, m), 4.49-4.32 (2H, m), 3.50-3.27 (1H, m), 3.11-2.92 (1H, m), 2.84-2.62 (2H, m), 2.46-2.11 (2H, m), 2.05-1.46 (5H, m), 1.92 (3H, s); Anal. Calcd for C24H26N4Cl2O9.H2O: C, 47.77; H, 4.68; N, 9.29. Found: C, 47.75; N, 4.59; N, 9.07. MS (ES+) 627/5/3 (M+K, 21%), 611/9/7 (M+Na, 87), 589/7/5 (M+ +1, 71), 266 (100); Accurate mass calculated for C24H27N4Cl2O9 (MH+): 585.1155. Found: 585.1134.

Sources & evidence

ORD record
ord-0919d1f8d338428eaab3152c9f1560ac
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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