Lithium hydroxide, monohydrate → HCID 58046701, compound

HRID 1751029Notes

Reaction equation

HRID 1751029 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3([CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][N:22]4[C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=5[S:24][C:23]4=[O:31])[CH2:15][CH2:14]3)[C:12](=[O:32])[N:11]([CH2:33][C:34]3[CH:35]=[C:36]([CH:41]=[CH:42][CH:43]=3)[C:37]([O:39]C)=[O:38])[CH2:10]2)=[CH:5][CH:4]=1.O.[OH-].[Li+]>CO.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3([CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][N:22]4[C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=5[S:24][C:23]4=[O:31])[CH2:15][CH2:14]3)[C:12](=[O:32])[N:11]([CH2:33][C:34]3[CH:35]=[C:36]([CH:41]=[CH:42][CH:43]=3)[C:37]([OH:39])=[O:38])[CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58046643HCID 58046643, compound

Product 1

HCID 58046701HCID 58046701, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-((1-(4-methoxyphenyl)-4-oxo-8-(3-(2-oxobenzo[d]thiazol-3(2H)-yl)propyl)-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.19 g, 0.32 mmol) in methanol (3 mL) was added lithium hydroxide monohydrate (0.027 g, 0.63 mmol) in water (1 mL). After stirring at room temperature for 18 h, the reaction mixture was concentrated in vacuo and isolated by preparatory TLC (10% methanol/dichloromethane) to obtain the title compound (0.11 g, 59%); 1H NMR (DMSO-d6): δ 1.64 (d, 2H, J=13.6 Hz), 1.79 (t, 2H, J=6.4 Hz), 1.88-1.95 (m, 2H), 2.38 (t, 2H, J=6 Hz), 2.50-2.66 (m, 4H), 3.69 (s, 3H), 3.97 (t, 2H, J=6.4 Hz), 4.53 (d, 4H, J=26.8 Hz), 6.86 (d, 2H, J=7.2 Hz), 6.94 (d, 2H, J=7.6 Hz), 7.16 (t, 1H, J=7.2 Hz), 7.30 (t, 1H, J=7.6 Hz), 7.38 (d, 1H, J=7.6 Hz), 7.47-7.53 (m, 2H), 7.58 (dd, 1H, J=8 and 1.2 Hz), 7.85-8.87 (m, 2H), 12.95 (br, 1H); MS for C32H34N4O5S m/z 587.02 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customisolated by preparatory TLC (10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-5bb83e62bdd9417d8a9bfb125e8cff57
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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