Lithium hydroxide, monohydrate → 1-{[(1R,10R,11S,16S)-3-hydroxy-1,11,15,15-tetramethyl-8,8-dioxo-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-5-yl]carbonyl}piperidine-4-carboxylic acid

HRID 422188Notes

Reaction equation

HRID 422188 reaction equation
[OH:1][C:2]1[CH:19]=[C:18]([C:20]([N:22]2[CH2:27][CH2:26][CH:25]([C:28]([O:30]C)=[O:29])[CH2:24][CH2:23]2)=[O:21])[CH:17]=[C:16]2[C:3]=1[C@@:4]1([CH3:37])[C@H:13]([CH2:14][S:15]2(=[O:33])=[O:32])[C@:12]2([CH3:34])[C@H:7]([C:8]([CH3:36])([CH3:35])[CH2:9][CH2:10][CH2:11]2)[CH2:6][CH2:5]1.O[Li].O>CO.O>[OH:1][C:2]1[CH:19]=[C:18]([C:20]([N:22]2[CH2:27][CH2:26][CH:25]([C:28]([OH:30])=[O:29])[CH2:24][CH2:23]2)=[O:21])[CH:17]=[C:16]2[C:3]=1[C@@:4]1([CH3:37])[C@H:13]([CH2:14][S:15]2(=[O:33])=[O:32])[C@:12]2([CH3:34])[C@H:7]([C:8]([CH3:36])([CH3:35])[CH2:9][CH2:10][CH2:11]2)[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58294858methyl 1-{[(1R,10R,11S,16S)-3-hydroxy-1,11,15,15-tetramethyl-8,8-dioxo-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-5-yl]carbonyl}piperidine-4-carboxylate

Product 1

HCID 532409481-{[(1R,10R,11S,16S)-3-hydroxy-1,11,15,15-tetramethyl-8,8-dioxo-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-5-yl]carbonyl}piperidine-4-carboxylic acidYield 64.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 1-{[(1R,10R,11S,16S)-3-hydroxy-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-5-yl]carbonyl}piperidine-4-carboxylate (97) (0.10 g, 0.18 mmol) and LiOH.H2O (0.10 g, 2.4 mmol) in MeOH (10 mL) and water (2.0 mL) was stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure and acidified with 1 M HCl. The resulting solid was collected by filtration to give 1-{[(1R,10R,11S,16S)-3-hydroxy-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-5-yl]carbonyl}piperidine-4-carboxylic acid (98) (0.06 g, 63%) as a white solid. 1H NMR (CD3OD): δ 7.29 (d, 1H), 6.97 (d, 1H), 4.43 (m, 1H), 3.70 (m, 1H), 3.58 (m, 1H), 3.36 (m, 2H), 3.26-2.96 (m, 4H), 2.62 (m, 1H), 2.24 9d, 1H), 2.10-1.16 (m, 13H), 1.09-0.99 (m, 5H), 0.90 (s, 3H), 0.88 (s, 3H). MS m/z 516 (C28H39NO6S−H+).

Workup

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

Sources & evidence

ORD record
ord-0fd0516a95b6419a85d66fe6800cb4ec
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

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