Water → HCID 131723610, compound

HRID 993039Notes

Reaction equation

HRID 993039 reaction equation
[S:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:18]([O:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:17]=1)=[O:15])=[O:11].[C:36](=O)([O:44]C1C=CC([N+]([O-])=O)=CC=1)[O:37][CH:38]([O:40][C:41](=[O:43])[CH3:42])[CH3:39].O>CN(C)C=O>[C:41]([O:40][CH:38]([O:37][C:36]([N:6]1[CH2:7][CH2:8][C:9]2[S:1][C:2]([C:10]([NH:12][CH2:13][C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:18]([O:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:17]=3)=[O:15])=[O:11])=[CH:3][C:4]=2[CH2:5]1)=[O:44])[CH3:39])(=[O:43])[CH3:42]

Participants

5

Reactant 3

HCID 962WaterHCID 117805601-acetoxyethyl p-nitrophenyl carbonateHCID 53793619HCID 53793619, compound

Product 1

HCID 131723610HCID 131723610, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 126 mg of diethyl [[4-[[[(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)carbonyl]amino]acetyl]-o-phenylen]dioxy]diacetate synthesized according to the method described in WO 9421599 in 3 ml of N,N-dimethylformamide was added 105 mg of 1-acetoxyethyl 4-nitrophenyl carbonate under stirring at room temperature, and the mixture was stirred at 40° C. for 20 hours. The reaction was poured into 3 ml of water, and extracted with 5 ml of ethyl acetate. The separated organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The residue thus obtained was purified by chromatography on an LH-20 column (chloroform:methanol=1:1) and a silica gel column (chloroform:acetone=8:1) to give the title compound (25.8 mg, 16%) as a free base.

Workup

  1. customsynthesized
  2. stirringthe mixture was stirred at 40° C. for 20 hours
  3. extractionextracted with 5 ml of ethyl acetate
  4. dry with materialThe separated organic layer was dried over magnesium sulfate
  5. customthe solvent was removed by distillation
  6. customThe residue thus obtained
  7. customwas purified by chromatography on an LH-20 column (chloroform:methanol=1:1)

Sources & evidence

ORD record
ord-3ccfbaa38f054c289493d2cc20b7386e
Source dataset
uspto-grants-2002_10
Patent number
US06472397B1

Reaction notes

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