Triethylamine → HCID 131723255, compound

HRID 2185503Notes

Reaction equation

HRID 2185503 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:18][OH:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:20][S:21](Cl)(=[O:23])=[O:22].C(N(CC)CC)C>CN(C)C=O>[S:21]([O:19][CH2:18][C@@H:9]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])(=[O:23])(=[O:22])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13969852HCID 13969852, compound

Product 1

HCID 131723255HCID 131723255, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The product from (A) (3.8 mmol) was dissolved in dimethylformamide (DMF) (20 mL) and the solution was cooled to 0° C. Methanesulfonyl chloride (14.4 mmol) and triethylamine At3N) (14.4 mmol) were added. The reaction was stirred at 0° C. for 2 hr, quenched with H2O (2×25 mL), saturated NaHCO3 (1×25 mL) and brine (1×25 mL). The organic layer was dried over Na2SO4, filtered and dried to give the title compound (1.2g, 92%) as a white solid: 1H NMR (400 MHz, CDCl3) δ 1.60 (9H, s), 1.91-2.05 (2H, m), 2.77-2.90 (2H, m), 3.68-3.82, 3.12 (3H, s), 3.9-4.05 (1H, m), 4.27-4.4 (2H, m), 4.72-4.82 (1H, m), 7.25-7.48 (5H, m).

Workup

  1. customquenched with H2O (2×25 mL), saturated NaHCO3 (1×25 mL) and brine (1×25 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-d02c540230b44c16a31d2c48a71185e9
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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