Ethyl Acetate → HCID 70167641, compound

HRID 906647Notes

Reaction equation

HRID 906647 reaction equation
[CH3:1][C:2]([N:4]([CH3:6])C)=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][C:18]2[S:22][C:21]([S:23](Cl)(=[O:25])=[O:24])=[CH:20][CH:19]=2)=[O:15])=[CH:10][CH:9]=1.C[CH2:28][O:29]C(C)=O>C(Cl)Cl.CN(C=O)C>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][C:18]2[S:22][C:21]([S:23]([N:4]3[CH2:2][CH2:1][C@@H:28]([OH:29])[CH2:6]3)(=[O:25])=[O:24])=[CH:20][CH:19]=2)=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31374DimethylacetamideHCID 27357135-((4-Chlorobenzamido)methyl)thiophene-2-sulfonyl chloride

Product 1

HCID 70167641HCID 70167641, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a suspension of R-3-pyrrolidinol hydrochloride (530 mg, 429 mmol) and DMA (0.75 ml, 14.3 mmol) in CH2Cl2/DMF 1:1 was added a solution of 5-({[1-(4-Chlorophenyl)-methanoyl]-amino}-methyl)-thiophene-2-sulfonyl chloride 1b (1.0 g, 2.86 mmol). At the end of addition the suspension disappeared. The reaction mixture was stirred overnight. 100 ml EtOAc were added and the excess of amine was extracted with HCl (1N), followed by washings with brine. The organic layers were dried over MgSO4 and evaporated to dryness to provide 351a (1.14 g, 99.9%) as a colourless foam: H1 NMR (DMSO d6) δ 9.34 (t, J=5.8 Hz, 1H), 7.89 (d, J=8.7 Hz, 2H), 7.49 (d, J=3.8 Hz, 1H), 7.55 (d, J=8.7 Hz, 2H), 7.13 (d, J=3.8 Hz, 1H), 4.95 (d, J=3.4 Hz, 1H), 4.65 (d, J=5.6 Hz, 2H), 4.16 (m, 1H), 3.40-3.20 (m, 5H), 3.00 (m, 1H), 3.35-3.23 (m, 3H), 1.80-1.60 (m, 2H), M/Z APCI: 401.2 (M+1), 398.9 (M−1).

Workup

  1. additionAt the end of addition the suspension
  2. extractionthe excess of amine was extracted with HCl (1N)
  3. washfollowed by washings with brine
  4. dry with materialThe organic layers were dried over MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-7d70a26abb294c46800b72efa1445ce0
Source dataset
uspto-grants-2011_09
Patent number
US08012995B1

Reaction notes

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