Sodium Carbonate → HCID 19787878, compound

HRID 1656536Notes

Reaction equation

HRID 1656536 reaction equation
[NH2:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH:13]([CH:20]([CH3:22])[CH3:21])[C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[O:11])[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:4][CH:3]=1.ClS([N:33]=[C:34]=[O:35])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(OCC)(=O)C>[O:8]=[C:7]1[N:6]([CH2:9][C:10]([NH:12][CH:13]([CH:20]([CH3:22])[CH3:21])[C:14](=[O:19])[C:15]([F:16])([F:18])[F:17])=[O:11])[C:5]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[N:4][CH:3]=[C:2]1[NH:1][C:34]([NH2:33])=[O:35]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 70918Chlorosulfonyl isocyanateHCID 19787906HCID 19787906, compound

Product 1

HCID 19787878HCID 19787878, compoundYield 13.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound from Example 6 (0.40 g) in tetrahydrofuran (10 mL) cooled to 0° C. was added dropwise chlorosulfonyl isocyanate (0.16 g) and the mixture was stirred for 45 min. The reaction mixture was neutralized with saturated aqueous sodium carbonate solution (3 mL), diluted with ethyl acetate (10 mL), and the separated organic phase was washed (water, brine). TLC examination revealed that the major reaction product was present in the aqueous phase. Following saturation of the aqueous phase with sodium chloride, repeated ethyl acetate extractions (4×25 mL) were performed. The combined organic layers were dried (magnesium sulfate) and evaporated. Chromatography with dichloromethane:tetrahydrofuran (10:1) as the eluent, followed by overnight drying (50° C., 27 Pa) gave the title compound (0.061 g) as an off-white solid; TLC: Rf =0.36, dichloromethane:methanol (10:1); NMR: 8.85 (d,1), 8.69 (s,1), 8.35 (s,1), 7.48 (m,5), 6.47 (broad s, 2), 4.70 (dd,1), 4.55 (dd,2), 2.2 (m,1), 0.89 (dd,6); MS: m/z=440(M+1).

Workup

  1. washthe separated organic phase was washed (water, brine)
  2. extractionethyl acetate extractions (4×25 mL)
  3. dry with materialThe combined organic layers were dried (magnesium sulfate)
  4. customevaporated
  5. waitChromatography with dichloromethane:tetrahydrofuran (10:1) as the eluent, followed by overnight
  6. customdrying (50° C., 27 Pa)

Sources & evidence

ORD record
ord-cf4b1bfe76f94c9b831e4fac9352d9d7
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

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