HCID 131720916, compound → HCID 131720915, compound

HRID 355471Notes

Reaction equation

HRID 355471 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C@@:19]3([CH2:27][O:26][C@H:25]([CH2:28][O:29][C:30]4[CH:35]=[CH:34][C:33]([C:36]5[CH:41]=[CH:40][C:39]([C:42]([O:44]C)=[O:43])=[CH:38][CH:37]=5)=[CH:32][CH:31]=4)[C@@H:23]([OH:24])[C@@H:21]3[OH:22])[OH:20])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=[O:4]>[OH-].[Na+].CO>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][C@@:19]3([CH2:27][O:26][C@H:25]([CH2:28][O:29][C:30]4[CH:35]=[CH:34][C:33]([C:36]5[CH:37]=[CH:38][C:39]([C:42]([OH:44])=[O:43])=[CH:40][CH:41]=5)=[CH:32][CH:31]=4)[C@@H:23]([OH:24])[C@@H:21]3[OH:22])[OH:20])=[CH:15][CH:16]=2)=[CH:9][CH:10]=1)([OH:4])=[O:2]

Participants

4

Reactant 1

HCID 131720916HCID 131720916, compound

Product 1

HCID 131720915HCID 131720915, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

0.67 g of 1,6-bis-O-(4'-methoxycarbonyl-biphenyl-4-yl)-2,5-O-methylene-D-mannitol was heated under reflux for 16 hours in 15 ml of concentrated sodium hydroxide solution and 15 ml of methanol; thereupon the mixture was evaporated and the residue was acidified with dilute hydrochloric acid. The precipitate of 1,6-bis-O-(4'-carboxy-biphenyl-4-yl)-2,5-O-methylene-D-mannitol which thereby formed was filtered off, dissolved in 5 ml of acetic anhydride and 5 ml of pyridine and stirred at room temperature for 16 hours. Now, the mixture was again evaporated, the residue was poured into dilute hydrochloric acid and the mixture was filtered; there was thus obtained 3,4-di-O-acetyl-1,6-bis-O-(4'-carboxy-biphenyl-4-yl)-2,5-O-methylene-D-mannitol in the form of colorless crystals, MS: m/z 669.4 ([M-H]-).

Workup

  1. customthereupon the mixture was evaporated

Sources & evidence

ORD record
ord-e5b068f29a2046ebada71ebd1847f9c8
Source dataset
uspto-grants-1998_11
Patent number
US05830920

Reaction notes

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