Ethanol → HCID 22283177, compound

HRID 2308474Notes

Reaction equation

HRID 2308474 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:13]([C:15]3[CH:38]=[CH:37][C:18]([CH2:19][N:20]([CH3:36])[CH2:21][CH2:22][O:23]C(=O)C4C=CC(OC)=C(OC)C=4)=[CH:17][CH:16]=3)=[O:14])[S:11][C:7]=2[C:6]([N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)=[CH:5][CH:4]=1.C(O)C>[OH-].[Na+].O>[OH:23][CH2:22][CH2:21][N:20]([CH2:19][C:18]1[CH:17]=[CH:16][C:15]([C:13]([NH:12][C:10]2[S:11][C:7]3[C:6]([N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[N:9]=2)=[O:14])=[CH:38][CH:37]=1)[CH3:36]

Participants

5

Reactant 2

HCID 702EthanolHCID 86584921HCID 86584921, compound

Product 1

HCID 22283177HCID 22283177, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

3,4-Dimethoxy-benzoic acid 2-{[4-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl carbamoyl)-benzyl]-methyl-amino}-ethyl ester (63 mg, 0.10 mmol) are heated in aqueous sodium hydroxide (1M, 0.5 ml) and ethanol (2 ml) to 100° C. for 30 min. The mixture is diluted with water and extracted twice with ethyl acetate. The combined organic layers are extracted with saturated aqueous sodium hydrogencarbonate, dried and evaporated to dryness. Flash chromatography (silica, eluent methylene chloride containing 5% methanol) affords the product as white crystals in 48% yield. MS: m/e=457 (M+H+).

Workup

  1. extractionextracted twice with ethyl acetate
  2. extractionThe combined organic layers are extracted with saturated aqueous sodium hydrogencarbonate
  3. customdried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-bbefaf89df6e4749b346596363ed783f
Source dataset
uspto-grants-2004_12
Patent number
US06835732B2

Reaction notes

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