Hydrochloric Acid → HCID 22467255, compound

HRID 1934620Notes

Reaction equation

HRID 1934620 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.O1C2C=CC(C(C3C4C(=CC(Cl)=CC=4)N(C)C=3)C(C3C=CC(CC(OCC)=O)=C(S(=O)(=O)N)C=3)=O)=CC=2OC1.Cl>O1CCCC1.C(OCC)(=O)C>[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 22467202HCID 22467202, compoundHCID 70160030HCID 70160030, compound

Product 1

HCID 22467255HCID 22467255, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

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-6c33495ebd634fba9db31a020139df1e
Source dataset
uspto-grants-2002_05
Patent number
US06384070B2

Reaction notes

Loading…