Sodium Hydroxide → 1-(cyclohexyl)methyl-3-[2-(hydroxymethyl)thiazol-4-yl]7-methoxy-1H-indole

HRID 644052Notes

Reaction equation

HRID 644052 reaction equation
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([C:19]3[N:20]=[C:21]([CH2:24][O:25]C(C(C)(C)C)=O)[S:22][CH:23]=3)=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([C:19]3[N:20]=[C:21]([CH2:24][OH:25])[S:22][CH:23]=3)=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 686987601-(cyclohexyl)methyl-7-methoxy-3-{2-[(tertbutylcarbonyloxy)methyl]thiazol-4-yl}-1H-indole

Product 1

HCID 686938831-(cyclohexyl)methyl-3-[2-(hydroxymethyl)thiazol-4-yl]7-methoxy-1H-indoleYield 73.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(cyclohexyl)methyl-7-methoxy-3-{2-[(tertbutylcarbonyloxy)methyl]thiazol-4-yl}-1H-indole (0.92 g, 2.10 mmol) was dissolved in methanol (20 ml) and 4N sodium hydroxide (5 ml) added. The solution was stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue taken up in dichloromethane. Water (10 ml) was added and the organic layer separated. The aqueous layer was extracted with dichloromethane and the combined organic layers concentrated in vacuo to yield 1-(cyclohexyl)methyl-3-[2-(hydroxymethyl)thiazol-4-yl]-7-methoxy-1H-indole as a pale orange foam (0.55 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionWater (10 ml) was added
  3. customthe organic layer separated
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. concentrationthe combined organic layers concentrated in vacuo

Sources & evidence

ORD record
ord-5c7e4137a8274a63a670e0f9c3b34444
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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