Chloroacetyl chloride → HCID 87546119, compound

HRID 1435700Notes

Reaction equation

HRID 1435700 reaction equation
O.Cl.[Cl:3][C:4]1[C:5]([CH3:26])=[C:6]([S:10]([NH:13][C:14]2[S:15][CH:16]=[C:17]([CH2:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][OH:25])[N:18]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1.Cl[CH2:28][C:29](Cl)=[O:30].[OH-].[K+]>O.C1COCC1>[Cl:3][C:4]1[C:5]([CH3:26])=[C:6]([S:10]([NH:13][C:14]2[S:15][CH:16]=[C:17]([CH2:19][CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][O:25][CH2:28][C:29]3=[O:30])[N:18]=2)(=[O:11])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14797Potassium Hydroxide2×HCID 87546947HCID 87546947, compound

Product 1

HCID 87546119HCID 87546119, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of EXAMPLE 208B (187 mg, 0.44 mmol) in H2O (2 mL)/THF (1 mL) was chloroacetyl chloride (110 mg, 0.97 mmol) in THF (3 mL) dropwise added under a period of 40 min. The temperature was kept at 8° C. and 2 M KOH was added continuously to adjust the pH to around 6-8. Aqueous potassium hydroxide (6 M, 0.38 mL, 1.41 mmol) was added and the mixture was stirred at room temperature for 20 min. The pH was adjusted to 8 and the mixture was extracted with ethyl acetate. The organic phase was separated and the solvent was evaporated. The residue was flash chromatographed on silica gel eluting with 30% acetone in DCM, yielding 98 mg (52 %) of the title compound: MS (Ionspray, [M+H]+) m/z 429. Anal. Calcd. (found) for C17H20ClN3O4S2: C, 47.5 (47.4)%; H, 4.7 (4.9)%; N, 9.8 (9.5)%.

Workup

  1. additiondropwise added under a period of 40 min
  2. customwas kept at 8° C.
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic phase was separated
  5. customthe solvent was evaporated
  6. customchromatographed on silica gel eluting with 30% acetone in DCM

Sources & evidence

ORD record
ord-368a0436e914412a98225d8aa882eafd
Source dataset
uspto-grants-2009_11
Patent number
US07618961B2

Reaction notes

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