Triethylamine → HCID 10389762, compound

HRID 1940044Notes

Reaction equation

HRID 1940044 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]([CH3:38])([O:10][C:11]([NH:13][C@H:14]([C:18]([N:20]1[CH2:37][CH2:36][CH2:35][C@H:21]1[C:22]([NH:24][CH:25]([CH:32]([CH3:34])[CH3:33])[CH:26]([OH:31])[C:27]([F:30])([F:29])[F:28])=[O:23])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[CH3:9].CCN(CC)CC>ClCl.C(Cl)Cl.CS(C)=O>[CH3:9][C:8]([CH3:7])([O:10][C:11]([NH:13][C@H:14]([C:18]([N:20]1[CH2:37][CH2:36][CH2:35][C@H:21]1[C:22]([NH:24][CH:25]([CH:32]([CH3:33])[CH3:34])[C:26](=[O:31])[C:27]([F:28])([F:29])[F:30])=[O:23])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[CH3:38]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 10073277HCID 10073277, compound

Product 1

HCID 10389762HCID 10389762, compoundYield 96.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolventHCID 24526ChlorineSolvent2×

Procedure

To a stirred solution of oxalyl chloride (0.31 mL, 3.56 mmol) in CH2 Cl2 (30 mL) cooled to -60° C. is added DMSO (0.51 mL, 7.12 mmol) dropwise. After 6 min, a solution of 49 (1.11 g, 2.37 mmol) in a mixture of CH2Cl2 (5 mL) and DMSO (3 mL) is slowly added and, 20 min later, Et3N (1.99 mL, 14.25 mmol) is added. The reaction mixture is allowed to warm to room temperature, diluted with CH2 Cl2 (100 mL) and washed with 0.5N aqueous HCl (2×150 mL), and half-saturated aqueous NaHCO3 (2×100 mL) followed by brine (75 mL). Drying (MgSO4) and concentration gives 50 (1.06 g, 96%, mixture of two diastereomers, ratio≈1:1) as a white foam.

Workup

  1. additionis slowly added and, 20 min later
  2. washwashed with 0.5N aqueous HCl (2×150 mL), and half-saturated aqueous NaHCO3 (2×100 mL)
  3. customDrying
  4. concentration(MgSO4) and concentration

Sources & evidence

ORD record
ord-5fd4fe0549954066a499edb29284cede
Source dataset
uspto-grants-1997_12
Patent number
US05698523

Reaction notes

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