Potassium Bromide → HCID 86757733, compound

HRID 1250830Notes

Reaction equation

HRID 1250830 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:49]=[CH:50][C:51]=1[Cl:52])[CH2:8][O:9][CH:10]1[O:15][CH:14]([CH2:16][O:17][C:18](=[O:27])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH:13]([O:28][CH:29]2[O:38][CH:37]3[CH:32]([O:33][CH:34]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[O:35][CH2:36]3)[CH:31]([OH:45])[CH:30]2[OH:46])[CH:12]([OH:47])[CH:11]1[OH:48])(=[O:3])[CH3:2].[K+].[Br-]>O>[C:14]([O:47][CH:12]1[CH:11]([O:48][C:18](=[O:17])[CH3:19])[CH:10]([O:9][CH2:8][C:7]2[CH:49]=[CH:50][C:51]([Cl:52])=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=2)[O:15][CH:14]([CH2:16][O:17][C:18](=[O:27])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH:13]1[O:28][CH:29]1[O:38][CH:37]2[CH:32]([O:33][CH:34]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[O:35][CH2:36]2)[CH:31]([O:45][C:8](=[O:9])[CH3:7])[CH:30]1[O:46][C:1](=[O:3])[CH3:2])(=[O:15])[CH3:13]

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 70146062HCID 70146062, compound

Product 1

HCID 86757733HCID 86757733, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared as a white foam (0.142 g, 81%) from 4-methoxy-benzoic acid 6-(3-acetylamino-4-chloro-benzyloxy)-3-(7,8-dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4,5-dihydroxy-tetrahydro-pyran-2-ylmethyl ester using a procedure similar to Example 25, mp >110° C. (decomp.); 1H NMR (DMSO-d6) δ1.94 (s, 3H), 1.95 (s, 3H), 1.98 (s, 3H), 1.99 (s, 3H), 2.06 (s, 3H), 3.61 (t, J=9.7 Hz, 1H), 3.68-3.75 (m, 1H), 3.80 (dd, J=4.6, 9.4 Hz, 1H), 3.82 (s, 3H), 3.82-3.89 (m, 1H), 4.11-4.16 (m, 1H), 4.17 (q, 9.7 Hz, 1H), 4.40 (dd, J=3.3, 12.3 Hz, 1H), 4.63 (ABq, J=12.7 Hz, Δδ=0.15, 2H), 4.64 (d, J=10.8 Hz, 1H), 4.77 (dd, J=7.9, 9.4 Hz, 1H), 4.86-4.91 (m, 2H), 5.26 (t, J=9.9 Hz, 1H), 5.32-5.38 (m, 2H), 5.54 (s, 1H), 7.06 (dt, J=2.9, 9.7 Hz, 3H), 7.29-7.37 (m, 5H), 7.42 (d, J=8.1 Hz, 1H), 7.61 (s, 1H), 7.99 (dt, J=2.9, 9.9 Hz, 2H), 9.4 (s, 1H); IR (KBr) 3400, 2950, 2840, 1755, 1700, 1600, 1580, 1535, 1515, 1450, 1420, 1375, 1240, 1165, 1110, 1070, 1055, and 1030 cm−1; mass spectrum [(+) FAB], m/z 914/916 (M+H)+, 936/938 (M+Na)+; Anal. Calcd. for C44H48ClNO18.1.0 H2O: C, 56.68; H, 5.41; N, 1.50, Found: C, 56.37; H, 5.08; N, 1.48.

Sources & evidence

ORD record
ord-5af235ad66e84f26b9d2b6c0bfa636ef
Source dataset
uspto-grants-2002_01
Patent number
US06340670B1

Reaction notes

Loading…