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 422188노트

반응식

HRID 422188 반응식
[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

참가 물질

5

반응물 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

생성물 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 acid수율 64.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-0fd0516a95b6419a85d66fe6800cb4ec
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101605B2

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