Sodium Hydroxide → HCID 86635525, compound

HRID 1253994Notes

Reaction equation

HRID 1253994 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11]([N:14]([CH2:19][C@H:20]3[O:24]C(C)(C)[N:22]([C:27]([O:29][C@@H:30]4[C@H:37]5[C@H:33]([O:34][CH2:35][CH2:36]5)[O:32][CH2:31]4)=[O:28])[C@H:21]3[CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=4)=[CH:41][CH:40]=3)[CH2:15][CH:16]([CH3:18])[CH3:17])(=[O:13])=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)(C)C.Cl>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11]([N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:19][C@H:20]([OH:24])[C@@H:21]([NH:22][C:27](=[O:28])[O:29][C@@H:30]3[C@H:37]4[C@H:33]([O:34][CH2:35][CH2:36]4)[O:32][CH2:31]3)[CH2:38][C:39]3[CH:40]=[CH:41][C:42]([O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=4)=[CH:43][CH:44]=3)(=[O:13])=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59997206HCID 59997206, compound

Product 1

HCID 86635525HCID 86635525, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

70 mg of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (4S,5R)-5-{[(2,3-dihydro-1,4-benzodioxin-6-ylsulfonyl)(isobutyl)amino]methy}-2,2-dimethyl-4-[4-(2-pyridinylmethoxy)benzyl]-1,3-oxazolidine-3-carboxylate were dissolved in 15 mL of isopropanol and 5 ml of concentrated hydrochloric acid. After 2 h, the reaction was treated with excess 3N sodium hydroxide and extracted with ethyl acetate. Evaporation of the solvent gave 67 mg of the desired product. 1H NMR: 08.3 (6H, dd), 1.4-1.8 (4H, m), 2.6-3.2 (7H, m), 3.6 (2H, m), 3.75 (2H, m), 3.9 (2H, m), 4.25 (4H, bs), 4.95 (1H, d), 5.0 (1H, m), 5.6 (1H, d), 6.9 (2H, d), 6.95 (2H, d), 7.1 (2H, d), 7.2 (2H, m), 7.45 (1H, d), 7.7 (1H, t), 8.58 (1H, d).

Workup

  1. extractionextracted with ethyl acetate
  2. customEvaporation of the solvent

Sources & evidence

ORD record
ord-65c94d02012d466eaf808ff50b536e34
Source dataset
uspto-grants-2013_06
Patent number
US08455497B2

Reaction notes

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