Water → HCID 20599063, compound

HRID 478935Notes

Reaction equation

HRID 478935 reaction equation
[C:1]([C@:9]1([OH:47])[C@@:16]([C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([OH:17])[C@:15]([C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([OH:26])[C@@H:14]([CH:35](S(C2C=CC(C)=CC=2)(=O)=O)[OH:36])[O:13][C@@H:10]1[O:11][CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:48]=[N+:49]=[N-:50].[Na+].O>CN(C=O)C>[C:1]([C@:9]1([OH:47])[C@@:16]([C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([OH:17])[C@:15]([C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([OH:26])[C@@H:14]([CH:35]([N:48]=[N+:49]=[N-:50])[OH:36])[O:13][C@@H:10]1[O:11][CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 54196577HCID 54196577, compound

Product 1

HCID 20599063HCID 20599063, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 g of compound 2 and 3 g of NaN3 were dissolved in 100 cc of DMF. Reaction was allowed to proceed for 24 hrs at 70° C. after which the reaction mass was poured into 1 liter of water. Compound 5, obtained as a solid, was recrystallized from acetone giving 8 g (quant.) after drying over P2O5. M.p. 111° C.; 1H NMR (CDCl3): δ 8.22, 8.07, 7.92 (d,d,d, 2H each, benzoyl), 7.38-7.66 (m, 9H, benzoyl), 6.0—5.96 (m, 2H, H2,3), 5.8 (m, 1H, H4), 5.13 (d, 1H, H1), 4.47 (m, 1H, H5), 3.69 (s, 3H, OMe), 3.62 (AB, 2H, H6.6′).

Workup

  1. customReaction

Sources & evidence

ORD record
ord-07e191775c214d8b920a6f31580b4766
Source dataset
uspto-grants-2003_11
Patent number
US06642365B1

Reaction notes

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