Hydrochloric Acid → HCID 57617112, compound

HRID 1360111Notes

Reaction equation

HRID 1360111 reaction equation
C(OC([NH:8][C@H:9]([C:14]([N:16]1[CH2:24][C@H:23]([O:25][C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[C:33]([CH:36]=[CH2:37])[CH:34]=3)[N:29]=[C:28]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:27]=2)[CH2:22][C@H:17]1[C:18]([O:20][CH3:21])=[O:19])=[O:15])[CH2:10][CH2:11][CH2:12][CH3:13])=O)(C)(C)C.Cl.CCN(C(C)C)C(C)C.[CH2:54]([S:59](Cl)(=[O:61])=[O:60])[CH2:55][CH2:56][CH:57]=[CH2:58]>CCOC(C)=O.CN(C=O)C>[CH2:54]([S:59]([NH:8][C@H:9]([C:14]([N:16]1[CH2:24][C@H:23]([O:25][C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[C:33]([CH:36]=[CH2:37])[CH:34]=3)[N:29]=[C:28]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:27]=2)[CH2:22][C@H:17]1[C:18]([O:20][CH3:21])=[O:19])=[O:15])[CH2:10][CH2:11][CH2:12][CH3:13])(=[O:61])=[O:60])[CH2:55][CH2:56][CH:57]=[CH2:58]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 14872245Pent-4-ene-1-sulfonyl chlorideHCID 57617109HCID 57617109, compound

Product 1

HCID 57617112HCID 57617112, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Compound 32 (115 mg, 0.196 mmol) was dissolved in EtOAc (5 mL) cooled to 0° C. and treated with anhydrous HCl gas for 10 min. The reaction mixture was then concentrated to give a solid. The solid was dissolved in DMF (2 mL) and DIPEA (0.1 mL, 0.57 mmol) was added. The reaction was cooled to 10° C. and 4-pentenesulfonyl chloride (35 mg, 0.20 mmol) (Culshaw, P. N.; Walton, J. C., J. Chem. Soc., Perkin Trans. 2 (1991), 8, p 1201) was then added. The mixture was stirred at RT for 30 min, quenched with aqueous NaHCO3 and extracted with EtOAc. The EtOAc extract was dried over NaSO4, filtered, concentrated to an oil and chromatographed on silica to give 33 (94 mg, 78% yield) as a foam. LRMS (M+1)+=620.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customto give a solid
  3. temperatureThe reaction was cooled to 10° C.
  4. customquenched with aqueous NaHCO3
  5. extractionextracted with EtOAc
  6. extractionThe EtOAc extract
  7. dry with materialwas dried over NaSO4
  8. filtrationfiltered
  9. concentrationconcentrated to an oil
  10. customchromatographed on silica

Sources & evidence

ORD record
ord-f4839fff8aa34f088bfd79735c46aeba
Source dataset
uspto-grants-2011_02
Patent number
US07879797B2

Reaction notes

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