Potassium Bromide → HCID 54011556, compound

HRID 1250833Notes

Reaction equation

HRID 1250833 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:52]=[CH:53][C:54]=1[Cl:55])[CH2:8][O:9][CH:10]1[O:15][CH:14]([CH2:16][O:17][C:18](=[O:30])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[CH:13]([O:31][CH:32]2[O:41][CH:40]3[CH:35]([O:36][CH:37]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[O:38][CH2:39]3)[CH:34]([OH:48])[CH:33]2[OH:49])[CH:12]([OH:50])[CH:11]1[OH:51])(=[O:3])[CH3:2].[K+].[Br-]>O>[C:14]([O:50][CH:12]1[CH:11]([O:51][C:18](=[O:17])[CH3:19])[CH:10]([O:9][CH2:8][C:7]2[CH:52]=[CH:53][C:54]([Cl:55])=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=2)[O:15][CH:14]([CH2:16][O:17][C:18](=[O:30])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[CH:13]1[O:31][CH:32]1[O:41][CH:40]2[CH:35]([O:36][CH:37]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[O:38][CH2:39]2)[CH:34]([O:48][C:8](=[O:9])[CH3:7])[CH:33]1[O:49][C:1](=[O:3])[CH3:2])(=[O:15])[CH3:13]

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 54333070(3,4-Dimethoxy-phenyl)-acetic 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

Product 1

HCID 54011556HCID 54011556, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared as a white foam (0.105 g, 89%) from (3,4-dimethoxy-phenyl)-acetic 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 >98° C. (decomp.); 1H NMR (DMSO-d6) δ1.92 (s, 3H), 1.94 (s, 3H), 1.97 (s, 3H), 1.99 (s, 3H), 2.07 (s, 3H), 3.62-3.77 (m, 4H), 3.66 (s, 3H), 3.67 (s, 3H), 3.89 (t, J=9.2 Hz, 2H), 3.99-4.03 (m, 1H), 4.10 (dd, J=10.5, 16.0 Hz, 1H), 4.19 (dd, J=4.4, 11.9 Hz, 1H), 4.44-4.50 (m, 2H), 4.64-4.70 (m, 2H), 4.84 (d, J=8.1 Hz, 1H), 4.87 (dd, J=4.0, 10.1 Hz, 1H), 5.21 (d, J=3.7 Hz, 1H), 5.25 (d, J=9.9 Hz, 1H), 5.30 (t, J=9.2 Hz, 1H), 5.62 (s, 1H), 6.77 (dd, J=1.8, 8.1 Hz, 1H), 6.81 (d, J=8.3 Hz, 1H), 6.86 (d, J=1.8 Hz, 1H), 7.04 (dd, J=1.8, 8.3 Hz, 1H), 7.35 (s, 5H), 7.44 (d, J=8.1 Hz, 1H), 7.61 (s, 1H), 9.51 (s, 1H); IR (KBr) 3370, 2930, 2860, 1755, 1690, 1600, 1520, 1450, 1420, 1370, 1240, 1140, 1055, and 1030 cm−1; mass spectrum [(+) FAB], m/z 958/960 (M+H)+, 980/982 (M+Na)+; Anal. Calcd. for C46H52ClNO19.1.75 H2O: C, 55.81; H, 5.65; N, 1.41, Found: C, 55.60; H, 5.14; N, 1.38.

Sources & evidence

ORD record
ord-110a3b16a4254d78a92cce972bb2742f
Source dataset
uspto-grants-2002_01
Patent number
US06340670B1

Reaction notes

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