Acetic Acid → HCID 10359496, compound

HRID 917346Notes

Reaction equation

HRID 917346 reaction equation
[C:1]([C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[S:5][C:4]=1[NH:12][C:13](=[O:19])[CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])#[N:2].[CH:20](=O)[CH:21]([CH3:23])[CH3:22].C(O)(=O)C.[Na]>ClCCl>[C:1]([C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][N:7]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:6]=2[S:5][C:4]=1[NH:12][C:13](=[O:19])[CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])#[N:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6561IsobutyraldehydeHCID 5360545SodiumHCID 58962826HCID 58962826, compound

Product 1

HCID 10359496HCID 10359496, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the material isolated in Step A in 2 mL of dichloromethane was added 0.041 mL (0.90 mmol) of iso-butyraldehyde, followed by 0.026 mL (0.45 mmol) of acetic acid and 0.10 g (0.45 mmol) of sodium tracetoxyborohydride. After 16 h at ambient temperature the reaction was diluted with 30 mL of dichloromethane and washed twice with equal volumes of saturated aqueous NaHCO3. The organic layer was dried (Na2SO4) and concentrated in vacuo. Purification by preparative reversed phase BPLC afforded the tide compound.

Workup

  1. washwashed twice with equal volumes of saturated aqueous NaHCO3
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by preparative reversed phase BPLC
  5. customafforded the tide compound

Sources & evidence

ORD record
ord-2a85ca6f47e34d43a076f96c3d704e3e
Source dataset
uspto-grants-2007_09
Patent number
US07273876B2

Reaction notes

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