Triethylamine → HCID 178523565, compound

HRID 898108Notes

Reaction equation

HRID 898108 reaction equation
N1C=CC=CC=1S[S:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[CH-:15][CH:16]=[CH:17][CH:18]=1)=[O:13].[CH-:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1.[Fe+2:24].C(S)[C@@H](O)[C@H](O)CS.CCN(CC)CC>CO>[SH:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[CH-:18][CH:17]=[CH:16][CH:15]=1)=[O:13].[CH-:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1.[Fe+2:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 446094D-1,4-DithiothreitolHCID 178523569HCID 178523569, compound

Product 1

HCID 178523565HCID 178523565, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 12 (113 mg, 0.28 mmol) dissolved in 6 mL of MeOH was added DTT (438 mg, 2.8 mmol) and Et3N (79 mL, 0.57 mmol). The solution was stirred at room temperature for 18 h, followed by evaporation of the solvent. The residue was dissolved in 15 mL of EtOAc and rinsed with H20 (8×15 mL) to remove excess DTT. After drying over MgSO4 and concentrating, the residue was purified by flash chromatography (hexanes/EtOAc, 1:1, v/v) to afford 46 mg (57%) of 13. 1H NMR 400 MHz (CDCl3) d 6.16 (br s, 1H), 4.66 (t, J=1.8 Hz, 2H), 4.33 (t, J=1.8 Hz, 2H), 4.19 (s, 5H), 3.53 (q, J=6.4 Hz, 2H), 2.75 (m, 2H).

Workup

  1. customfollowed by evaporation of the solvent
  2. dissolutionThe residue was dissolved in 15 mL of EtOAc
  3. washrinsed with H20 (8×15 mL)
  4. customto remove excess DTT
  5. dry with materialAfter drying over MgSO4
  6. concentrationconcentrating
  7. customthe residue was purified by flash chromatography (hexanes/EtOAc, 1:1

Sources & evidence

ORD record
ord-e52a8b79c6af49b7bdd19412933cf5cb
Source dataset
uspto-grants-2008_04
Patent number
US07351575B2

Reaction notes

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