Water → HCID 178437734, compound

HRID 1419805Notes

Reaction equation

HRID 1419805 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[C:9]([NH:16][C@H:17]2[CH2:22][CH2:21][C@@H:20]([CH2:23][OH:24])[CH2:19][CH2:18]2)=[N:10][CH:11]=[N:12][C:13]=1[CH2:14][CH3:15].C(N(CC)CC)C.O>ClCCl.CS(C)=O>[Cl:7][C:8]1[C:9]([NH:16][C@H:17]2[CH2:22][CH2:21][C@@H:20]([CH:23]=[O:24])[CH2:19][CH2:18]2)=[N:10][CH:11]=[N:12][C:13]=1[CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178437735HCID 178437735, compound

Product 1

HCID 178437734HCID 178437734, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent3×

Procedure

6.7 g (86 mmol) of DMSO in 17 ml of dichloromethane were added under N2 to a solution of 5.5 g (43 mmol) of oxalyl chloride in 50 ml of dichloromethane at -78° C. After 5 minutes, a solution of 10.6 g (39 mmol) of the hydroxymethyl compound from Example 3 in 5.3 ml each of DMSO and dichloromethane was added, and the mixture was stirred for 1 hour at the temperature indicated. 35.6 g (350 mmol) of triethylamine were added dropwise. After 20 minutes, the mixture was allowed to warm to room temperature, 105 ml of H2O were added, extraction was carried out with dichloromethane, and removal of the solvent gave 9.5 g (35.5 mmol =91%) of the aldehyde as a white solid: m.p. 96° to 97° C.

Workup

  1. waitAfter 20 minutes
  2. extractionextraction
  3. customwas carried out with dichloromethane, and removal of the solvent

Sources & evidence

ORD record
ord-76ceeb33c2564f8a83a7857a6ff8feb5
Source dataset
uspto-grants-1999_03
Patent number
US05889012

Reaction notes

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