Hydrochloric Acid → HCID 68541943, compound

HRID 1445716Notes

Reaction equation

HRID 1445716 reaction equation
C[O:2][C:3]([C@@H:5]1[CH:14]=[C:13]2[C@@H:8]([CH2:9][C:10]3[C:11]4[C:18]([NH:19][CH:20]=3)=[CH:17][CH:16]=[CH:15][C:12]=42)[N:7]([C:21](=[O:29])[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:6]1)=[O:4].CO.[OH-].[Li+].Cl>O.CO.ClCCl.C1COCC1>[C:23]1([NH:22][C:21]([N:7]2[C@H:8]3[C:13]([C:12]4[CH:15]=[CH:16][CH:17]=[C:18]5[C:11]=4[C:10](=[CH:20][NH:19]5)[CH2:9]3)=[CH:14][C@@H:5]([C:3]([OH:4])=[O:2])[CH2:6]2)=[O:29])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 68545203HCID 68545203, compound

Product 1

HCID 68541943HCID 68541943, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a 100 ml round-bottom flask containing (6aR,9R)-7-phenylcarbamoyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid methyl ester (0.8 g, 2.06 mmol) is added methanol (12 ml), THF (24 ml) and a solution of lithium hydroxide (247 mg) in water (12 ml). The reaction mixture is stirred at room temperature for 20 minutes by which time TLC in 20% methanol/dichloromethane showed complete conversion of starting material. The colour of the crude reaction mixture has changed from light yellow to a violet red. The volatiles are removed in vacuo (leaving only water) and the aqueous solution made acidic with the addition of 1 M HCl. The resulting beige precipitate is filtered at the pump and the filter cake washed with distilled water (50 ml). The filter cake is then dried in a high vacuum oven at 50° C. for 16 hours providing product.

Workup

  1. customThe colour of the crude reaction mixture
  2. customThe volatiles are removed in vacuo (
  3. customleaving only water) and the aqueous solution
  4. filtrationThe resulting beige precipitate is filtered at the pump
  5. washthe filter cake washed with distilled water (50 ml)
  6. customThe filter cake is then dried in a high vacuum oven at 50° C. for 16 hours
  7. customproviding product

Sources & evidence

ORD record
ord-2a83e35925d0468c8f756b8399d91ee6
Source dataset
uspto-grants-2010_02
Patent number
US07666877B2

Reaction notes

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