Ethanol → HCID 22283177, compound

HRID 2250708Notes

Reaction equation

HRID 2250708 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-1461c4680eca4066b6d1d0e1bc39e55e
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

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