Potassium Bromide → HCID 86757734, compound

HRID 1250831Notes

Reaction equation

HRID 1250831 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:48]=[CH:49][C:50]=1[Cl:51])[CH2:8][O:9][CH:10]1[O:15][CH:14]([CH2:16][O:17][C:18](=[O:26])[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH:13]([O:27][CH:28]2[O:37][CH:36]3[CH:31]([O:32][CH:33]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[O:34][CH2:35]3)[CH:30]([OH:44])[CH:29]2[OH:45])[CH:12]([OH:46])[CH:11]1[OH:47])(=[O:3])[CH3:2].[K+].[Br-]>O>[C:14]([O:46][CH:12]1[CH:11]([O:47][C:18](=[O:17])[CH3:19])[CH:10]([O:9][CH2:8][C:7]2[CH:48]=[CH:49][C:50]([Cl:51])=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=2)[O:15][CH:14]([CH2:16][O:17][C:18](=[O:26])[C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)[CH:13]1[O:27][CH:28]1[O:37][CH:36]2[CH:31]([O:32][CH:33]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[O:34][CH2:35]2)[CH:30]([O:44][C:8](=[O:9])[CH3:7])[CH:29]1[O:45][C:1](=[O:3])[CH3:2])(=[O:15])[CH3:13]

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 70146170HCID 70146170, compound

Product 1

HCID 86757734HCID 86757734, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared as a white foam (0.225 g, 72%) from 4-chloro-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 114-115° C.; 1H NMR (DMSO-d6) δ1.94 (s, 3H), 1.95 (s, 3H), 1.98 (s, 3H), 1.99 (s, 3H), 2.05 (s, 3H), 3.62 (t, J=9.2 Hz, 1H), 3.68-3.74 (m, 1H), 3.79 (dd, J=4.2, 9.2 Hz, 1H), 3.86 (t, J=9.4 Hz, 1H), 4.13-4.19 (m, 1H), 4.18 (q, J=9.4, 1H), 4.47 (dd, J=3.5, 12.3 Hz, 1H), 4.63 (ABq, J=12.7 Hz, Δδ=0.14, 2H), 4.66 (d, J=10.8 Hz, 1H), 4.79 (dd, J=8.1, 9.2 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), 7.05 (dd, J=1.8, 8.3 Hz, 1H), 7.27-7.31 (m, 2H), 7.32-7.36 (m, 3H), 7.42 (d, J=8.3 Hz, 1H), 7.58-7.63 (m, 3H), 8.02-8.06 (m, 2H), 9.49 (s, 1H); IR (KBr) 3410, 2950, 2860, 1755, 1690, 1600, 1530, 1450, 1420, 1375, 1260, 1140, 1070, 1055, and 1030 cm−1; mass spectrum [(+) FAB], m/z 918/920/922 (M+H)+, 940/942/944 (M+Na)+; Anal. Calcd. for C43H45Cl2NO17.1.0 H2O: C, 55.13; H, 5.06; N, 1.50, Found: C, 54.77; H, 4.73; N, 1.45.

Sources & evidence

ORD record
ord-dbd79abe2c03467b9bde3def7118a4cb
Source dataset
uspto-grants-2002_01
Patent number
US06340670B1

Reaction notes

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