Dimethylformamide → HCID 22907170, compound

HRID 742037Notes

Reaction equation

HRID 742037 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:13]2([C:19](O)=[O:20])[CH2:18][CH2:17][S:16][CH2:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.CN(C)C=O.C(Cl)(=O)C(Cl)=O.Cl.[NH2:41][OH:42].C(N(CC)CC)C>C(Cl)Cl.O1CCCC1.O>[OH:42][NH:41][C:19]([C:13]1([N:12]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18][CH2:17][S:16][CH2:15][CH2:14]1)=[O:20]

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 22907071HCID 22907071, compound

Product 1

HCID 22907170HCID 22907170, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 4-[[4-methoxybenzenesulfonyl](benzyl)amino]-4-carboxy-tetrahydrothiopyran (413.0 mg, 1.0 mmol) in methylene chloride (10 mL) containing dimethylformamide (80.0 mg, 1.1 mmol) is added a 2N solution of oxalyl chloride in methylene chloride (1.0 ml, 2.0 mmol) at -10° C. The mixture is allowed to warm to 20° C. for 30 minutes. This mixture is added to a pre-stirred mixture of hydroxylamine hydrochloride (280.0 mg, 4.0 mmol) in tetrahydrofuran (10 ml)/water (1 ml) containing triethylamine (650.0 mg, 6.0 mmol) at 0° C. dropwise. The reaction mixture is allowed to slowly warm to room temperature and stirring is continued for 1.5 days. The reaction is worked up by partitioning between 1N hydrochloric acid and ethyl acetate. The aqueous layer is removed and repeatedly extracted with ethyl acetate. The combined organic layers am dried (Na2SO4) and the solvent is evaporated. The crude product is purified by silica gel chromatography (2% methanol/methylene chloride) to give 4-[N-hydroxy-carbamoyl]-4-[[4-methoxybenzenesulfonyl](benzyl)amino]-tetrahydrothiopyran, m.p. 179°-181° C.

Workup

  1. temperatureto slowly warm to room temperature
  2. customby partitioning between 1N hydrochloric acid and ethyl acetate
  3. customThe aqueous layer is removed
  4. extractionrepeatedly extracted with ethyl acetate
  5. dry with materialThe combined organic layers am dried (Na2SO4)
  6. customthe solvent is evaporated
  7. customThe crude product is purified by silica gel chromatography (2% methanol/methylene chloride)

Sources & evidence

ORD record
ord-d4eaac451c4545c2898fea6929beb3ed
Source dataset
uspto-grants-1996_09
Patent number
US05552419

Reaction notes

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