Oxalyl chloride → HCID 22644965, compound

HRID 1976496Notes

Reaction equation

HRID 1976496 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([N:15]1[CH2:21][CH2:20][CH:19]([C:22]([OH:24])=O)[N:18]([S:25]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]#[C:37][CH3:38])=[CH:30][CH:29]=2)(=[O:27])=[O:26])[CH2:17][CH2:16]1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[NH2:40][OH:41].C(=O)(O)[O-].[Na+]>ClCCl.CN(C)C=O.O1CCCC1.O.C(OCC)(=O)C.C(N(CC)CC)C>[C:7]([N:15]1[CH2:21][CH2:20][CH:19]([C:22]([NH:40][OH:41])=[O:24])[N:18]([S:25]([C:28]2[CH:29]=[CH:30][C:31]([O:34][CH2:35][C:36]#[C:37][CH3:38])=[CH:32][CH:33]=2)(=[O:27])=[O:26])[CH2:17][CH2:16]1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

11

Reactant 4

HCID 65578Oxalyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 22644873HCID 22644873, compound

Product 1

HCID 22644965HCID 22644965, compoundYield 103.4%

Reagents, catalysts & solvents 6

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To oxalyl chloride (0.72 mL of a 2 M solution in dichloromethane) in dichloromethane (1 mL) at 0° C. was added dimethylformamide (0.11 mL). After 15 min a solution of 1-benzoyl-4-{[4-(2-butynyloxy)phenyl]sulfonyl}-1,4-diazepane-5-carboxylic acid (0.328 g, 0.718 mmol) in dimethylformamide was added and the resulting reaction mixture was stirred at room temperature for 1h In a separate flask, 1.5 mL of triethylamine was added to a 0° C. mixture of 0.50 g of hydroxylamine hydrochloride in 15.4 mL of tetrahydrofuran and 3.8 mL of water. After this mixture stirred for 15 min at 0° C., the acid chloride solution was added to it in one portion and the resulting solution was allowed to warn to room temperature and stirred for another 18h. Ethyl acetate and aqueous sodium bicarbonate were then added to the reaction flask The organic phase was washed with aqueous sodium bicarbonate (3×) and dried over anhydrous potassium carbonate. Concentration in vacuo gave a thick gum (0.35 g) which was chromatographed on silica gel eluting with dichloromethane/methanol to give an off-white foam (0.22 g) which was triturated with diethyl ether to give 1-benzoyl-{[4-{[4-(2-butynyloxy)phenyl]sulfonyl}-N-hydroxy-1,4-diazepane-5-carboxamide as an off white powder (0.173 g). Electrospray Mass Spec 472.3(M+H)+.

Workup

  1. customthe resulting reaction mixture
  2. customto warn to room temperature
  3. stirringstirred for another 18h
  4. washwas washed with aqueous sodium bicarbonate (3×)
  5. dry with materialdried over anhydrous potassium carbonate
  6. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-373d9d18634c49c0997bf639966f0b86
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

Loading…