Lithium hydroxide, monohydrate → 3-[2-{2-[(tert-butoxycarbonyl)amino]phenyl}-3-cyclohexyl-6-(methoxycarbonyl)-1H-indol-1-yl]propanoic acid

HRID 1444628Notes

Reaction equation

HRID 1444628 reaction equation
O.[OH-].[Li+].[C:4]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[N:19]([CH2:37][CH2:38][C:39]([O:41]C)=[O:40])[C:20]2[C:25]([C:26]=1[CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[CH:24][CH:23]=[C:22]([C:33]([O:35][CH3:36])=[O:34])[CH:21]=2)=[O:10])([CH3:7])([CH3:6])[CH3:5]>C1COCC1.O>[C:4]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[N:19]([CH2:37][CH2:38][C:39]([OH:41])=[O:40])[C:20]2[C:25]([C:26]=1[CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1)=[CH:24][CH:23]=[C:22]([C:33]([O:35][CH3:36])=[O:34])[CH:21]=2)=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68693096Methyl 2-{2-[(tert-butoxycarbonyl)amino]phenyl}-3-cyclohexyl-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate

Product 1

HCID 686932213-[2-{2-[(tert-butoxycarbonyl)amino]phenyl}-3-cyclohexyl-6-(methoxycarbonyl)-1H-indol-1-yl]propanoic acidYield 81%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

1.1 eq of lithium hydroxide monohydrate was added to a solution of methyl 2-{2-[(tert-butoxycarbonyl) amino]phenyl}-3-cyclohexyl-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate in a mixture THF:H2O (4:1; 0.1 M). The mixture was stirred at RT for 1.5 h. The reaction was quenched with 1 N HCl and the solvent evaporated in vacuo. The residue was washed with the minimum amount of Et2O and the resultant precipitate filtered to obtain the title compound as a white solid (81%); MS (ES+) m/z 521 (M+H)+.

Workup

  1. customThe reaction was quenched with 1 N HCl
  2. customthe solvent evaporated in vacuo
  3. washThe residue was washed with the minimum amount of Et2O
  4. filtrationthe resultant precipitate filtered

Sources & evidence

ORD record
ord-2615390521444e52aaa76449f941883c
Source dataset
uspto-grants-2010_02
Patent number
US07662809B2

Reaction notes

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