Water → 4-(3-(Benzyloxycarbonylamino)-2-methylphenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxylic acid

HRID 2361346Notes

Reaction equation

HRID 2361346 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:42])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)[CH:28]=4)[NH:23][C:22]=3[C:21]([C:37]([O:39]CC)=[O:38])=[N:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].O>CO.C1COCC1>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:42])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([N:31]5[CH2:32][CH2:33][O:34][CH2:35][CH2:36]5)[CH:28]=4)[NH:23][C:22]=3[C:21]([C:37]([OH:39])=[O:38])=[N:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 67994745Ethyl 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxylate

Product 1

HCID 679949964-(3-(Benzyloxycarbonylamino)-2-methylphenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxylic acidYield 87.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a light orange, homogeneous solution of ethyl 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxylate (0.1705 g, 0.302 mmol) in methanol (3.59 mL) and THF (10.78 mL) was added LiOH (0.029 g, 1.208 mmol) in water (5.44 μL, 0.302 mmol). After 1.5 hr, the reaction was concentrated in vacuo. Water was added to the residue and acidified to pH ˜6 with 1 N aqueous HCl. The insoluble material was filtered and dried over Drierite to give the desired product (0.14098 g, 0.263 mmol, 87% yield) as an orange solid.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. additionWater was added to the residue
  3. filtrationThe insoluble material was filtered
  4. dry with materialdried over Drierite

Sources & evidence

ORD record
ord-541d6b323d3d4633abc216323e1eb27e
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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