Acetic Acid → benzyl 4-((5-(3-(1-hydroxyethyl)-1-oxo-1H-isochromen-4-yl)thiophen-2-yl)methyl)piperazine-1-carboxylate

HRID 634369Notes

Reaction equation

HRID 634369 reaction equation
[OH:1][CH:2]([C:4]1[O:5][C:6](=[O:21])[C:7]2[C:12]([C:13]=1[C:14]1[S:18][C:17]([CH:19]=O)=[CH:16][CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3].C(O)(=O)C.[N:26]1([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[Na].C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:1][CH:2]([C:4]1[O:5][C:6](=[O:21])[C:7]2[C:12]([C:13]=1[C:14]1[S:18][C:17]([CH2:19][N:29]3[CH2:30][CH2:31][N:26]([C:32]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[O:33])[CH2:27][CH2:28]3)=[CH:16][CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 643495Benzyl piperazine-1-carboxylateHCID 5360545SodiumHCID 1181311385-(3-(1-hydroxyethyl)-1-oxo-1H-isochromen-4-yl)thiophene-2-carbaldehyde2×

Product 1

HCID 118131376benzyl 4-((5-(3-(1-hydroxyethyl)-1-oxo-1H-isochromen-4-yl)thiophen-2-yl)methyl)piperazine-1-carboxylateYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 250 ml round bottomed flask 5-(3-(1-hydroxyethyl)-1-oxo-1H-isochromen-4-yl)thiophene-2-carbaldehyde (Intermediate B37) (780 mg, 2.60 mmol) was dissolved in 30 ml of DCM then acetic acid (0.446 ml, 7.79 mmol) and benzyl piperazine-1-carboxylate (1.503 ml, 7.79 mmol) were added. After few minutes sodium triacetoxyhydroborate (2.75 g, 12.99 mmol) was added and the mixture was stirred at r.t. The mixture was poured into 100 ml of DCM and 100 NaHCO3 sat. sol. then phases were separated and the organic one was concentrated to dryness to leave a brown oil that was immediately purified by chromatography eluting with Hexane\EtOAc mixtures to leave the title compound (903 mg, 1.790 mmol, 68.9% yield) as a yellow oil.

Workup

  1. addition(2.75 g, 12.99 mmol) was added
  2. customphases were separated
  3. concentrationthe organic one was concentrated to dryness
  4. customto leave a brown oil that
  5. customwas immediately purified by chromatography
  6. washeluting with Hexane\EtOAc mixtures

Sources & evidence

ORD record
ord-f666cc18edab4e689103cddd36290359
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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