Hydrochloric Acid → HCID 22467255, compound

HRID 369343Notes

Reaction equation

HRID 369343 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH:16]([C:35]3[C:43]4[C:38](=[CH:39][C:40]([Cl:44])=[CH:41][CH:42]=4)[N:37]([CH3:45])[CH:36]=3)[C:17]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][C:30](OCC)=[O:31])=[CH:25][CH:24]=3)(=[O:22])=[O:21])=[O:18])=[CH:15][C:10]=2[O:9][CH2:8]1.C(OCC)(=O)C.Cl>O1CCCC1>[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH:16]([C:35]3[C:43]4[C:38](=[CH:39][C:40]([Cl:44])=[CH:41][CH:42]=4)[N:37]([CH3:45])[CH:36]=3)[C:17]([NH:19][S:20]([C:23]3[CH:24]=[CH:25][C:26]([CH2:29][CH2:30][OH:31])=[CH:27][CH:28]=3)(=[O:22])=[O:21])=[O:18])=[CH:15][C:10]=2[O:9][CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 22467202HCID 22467202, compound

Product 1

HCID 22467255HCID 22467255, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (6 mg, 0.16 mmol) was added to a stirred solution of ethyl 2-(4-[2-(1,3-benzodioxol-5-yl)-2-(6-chloro-1-methyl-1H-3-indolyl)acetyl]sulfamoylphenyl)acetate (the product of Example 89, 80 mg, 0.14 mmol) in tetrahydrofuran (6 ml) at 0° C. under a nitrogen atmosphere. After 40 mins ethyl acetate (1 ml) was slowly added and the reaction mixture was poured into hydrochloric acid (50 ml). The product was extracted into ethyl acetate (2×50 ml), dried (MgSO4) and concentrated. Recrystallisation (methanol/ether) gave the product as a white crystalline solid (50 mg).

Workup

  1. extractionThe product was extracted into ethyl acetate (2×50 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customRecrystallisation (methanol/ether)

Sources & evidence

ORD record
ord-316e8b67f6854736874779402b1992e7
Source dataset
uspto-grants-2000_10
Patent number
US06136843

Reaction notes

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