Lithium hydroxide, monohydrate → HCID 53240854, compound

HRID 422181Notes

Reaction equation

HRID 422181 reaction equation
[OH:1][C:2]1[CH:19]=[C:18]2[C:5]([C@@:6]3([CH3:25])[C@H:15]([CH2:16][S:17]2(=[O:21])=[O:20])[C@:14]2([CH3:22])[C@H:9]([C:10]([CH3:24])([CH3:23])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]3)=[C:4]([C:26]([NH:28][CH2:29][C:30]([O:32]C)=[O:31])=[O:27])[CH:3]=1.O[Li].O>CO.O>[OH:1][C:2]1[CH:19]=[C:18]2[C:5]([C@@:6]3([CH3:25])[C@H:15]([CH2:16][S:17]2(=[O:21])=[O:20])[C@:14]2([CH3:22])[C@H:9]([C:10]([CH3:23])([CH3:24])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]3)=[C:4]([C:26]([NH:28][CH2:29][C:30]([OH:32])=[O:31])=[O:27])[CH:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58294849HCID 58294849, compound

Product 1

HCID 53240854HCID 53240854, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 2-{[(1R,10R,11S,16S)-5-hydroxy-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-yl]formamido}acetate (90) (0.13 g, 0.27 mmol) and LiOH.H2O (0.07 g, 2 mmol) in MeOH (10 mL) and water (10 mL) was stirred at room temperature for 18 h. The mixture was concentrated under reduced pressure and the aqueous residue was acidified with 1 M HCl. The resulting solid was collected by filtration to give 2-{[(1R,10R,11S,16S)-5-hydroxy-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-yl]formamido}acetic acid (91) (0.09 g, 72%) as a brown solid. 1H NMR (CD3OD): δ 8.82 (m, 1H), 7.24 (d, 1H), 7.03 (d, 1H), 4.06 (m, 2H), 3.47 (m 2H), 2.76 (d, 1H), 2.11 (d, 1H), 1.88-1.38 (m, 10H), 1.20 (m, 1H), 1.00 (m, 5H), 0.89 (s, 3H), 0.86 (s, 3H). MS m/z 464 (C24H33NO6S+H+).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-5b7daa159a0f4573b75d1d576d76712a
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

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