Potassium Bromide → HCID 54048238, compound

HRID 1250832Notes

Reaction equation

HRID 1250832 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:54]=[CH:55][C:56]=1[Cl:57])[CH2:8][O:9][CH:10]1[O:15][CH:14]([CH2:16][O:17][C:18](=[O:32])[CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]([O:33][CH:34]2[O:43][CH:42]3[CH:37]([O:38][CH:39]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[O:40][CH2:41]3)[CH:36]([OH:50])[CH:35]2[OH:51])[CH:12]([OH:52])[CH:11]1[OH:53])(=[O:3])[CH3:2].[K+].[Br-]>O>[C:14]([O:52][CH:12]1[CH:11]([O:53][C:18](=[O:17])[CH3:19])[CH:10]([O:9][CH2:8][C:7]2[CH:54]=[CH:55][C:56]([Cl:57])=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=2)[O:15][CH:14]([CH2:16][O:17][C:18](=[O:32])[CH:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:13]1[O:33][CH:34]1[O:43][CH:42]2[CH:37]([O:38][CH:39]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[O:40][CH2:41]2)[CH:36]([O:50][C:8](=[O:9])[CH3:7])[CH:35]1[O:51][C:1](=[O:3])[CH3:2])(=[O:15])[CH3:13]

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 70167039HCID 70167039, compound

Product 1

HCID 54048238HCID 54048238, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared as a white foam (0.289 g, 76%) from diphenyl-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 >99° C. (decomp.); 1H NMR (DMSO-d6) δ1.92 (s, 3H), 1.94 (s, 3H), 1.96 (s, 3H), 1.99 (s, 3H), 2.08 (s, 3H), 3.66 (t, J=9.9 Hz, 1H), 3.72-3.78 (m, 1H), 3.78 (t, J=9.0 Hz, 1H), 3.87 (t, J=9.7 Hz, 1H), 3.98-4.05 (m, 2H), 4.18-4.24 (m, 1H), 4.44 (ABq, J=12.7 Hz, Δδ=0.16, 2H), 4.61-4.67 (m, 2H), 4.80 (d, J=7.9 Hz, 1H), 4.88 (dd, J=4.2, 10.3 Hz, 1H), 5.16 (d, J=4.0 Hz, 1H), 5.22 (t, J=9.9 Hz, 1H), 5.29 (t, J=9.2 Hz, 1H), 5.31 (s, 1H), 5.60 (s, 1H), 6.99 (dd, J=1.5, 8.1 Hz, 1H), 7.20-7.25 (m, 2H), 7.27-7.35 (m, 8H), 7.35 (s, 5H), 7.43 (d, J=8.1 Hz, 1H), 7.59 (s, 1H), 9.51 (s, 1H); IR (KBr) 3410, 3070, 3025, 2930, 2860, 1755, 1690, 1600, 1525, 1450, 1410, 1375, 1240, 1140, 1055, and 1030 cm−1; mass spectrum [(+) FAB], m/z 974 (M+H)+, 996 (M+Na)+; Anal. Calcd. for C50H52ClNO17.1.25 H2O: C, 60.24; H, 5.51; N, 1.40, Found: C, 59.97; H, 5.10; N, 1.37.

Sources & evidence

ORD record
ord-8d1122cd3a834eaf9597980e6208e62a
Source dataset
uspto-grants-2002_01
Patent number
US06340670B1

Reaction notes

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