Hydrochloric Acid → HCID 86651922, compound

HRID 417788Notes

Reaction equation

HRID 417788 reaction equation
C([S:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:74]=[CH:73][C:20]([C:21]([O:23][C:24]2[CH:72]=[CH:71][C:27]([C:28]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([O:37][C:38](=[O:70])[C:39]4[CH:44]=[CH:43][C:42]([O:45][C:46](=[O:69])[C:47]5[CH:52]=[CH:51][C:50]([O:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][S:65]C(=O)C)=[CH:49][CH:48]=5)=[CH:41][CH:40]=4)[CH:32]=3)=[O:29])=[CH:26][CH:25]=2)=[O:22])=[CH:19][CH:18]=1)(=O)C.Cl>C1COCC1.CO.O>[SH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([O:23][C:24]2[CH:72]=[CH:71][C:27]([C:28]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([O:37][C:38](=[O:70])[C:39]4[CH:44]=[CH:43][C:42]([O:45][C:46](=[O:69])[C:47]5[CH:48]=[CH:49][C:50]([O:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][SH:65])=[CH:51][CH:52]=5)=[CH:41][CH:40]=4)[CH:32]=3)=[O:29])=[CH:26][CH:25]=2)=[O:22])=[CH:73][CH:74]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86651923HCID 86651923, compound

Product 1

HCID 86651922HCID 86651922, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Compound BC4 (0.2 g, 0.2 mmol) was dissolved in 50:50 THF/MeOH (20 mL), and following addition of 3 mL conc. HCl to the flask, the mixture was heated to reflux for 6 hours. The mixture was let to cool to room temperature, diluted with water (10 mL), and extracted with CH2Cl2 (2×200 mL). The solvent was removed, and the residue purified by column chromatography (CH2Cl2: EtOH, 10:0.03). The product was then selectively precipitated from CH2Cl2 through dropwise addition of petroleum ether. Yield 0.11 g (60%). EA: Found: C, 69.37; H, 7.21. C56H66O10S2 requires C, 69.83; H, 6.91%. 1H NMR: δH (CDCl3; 300 MHz): 1.24-1.56 (30 H, m, CH2 / SH), 1.63 (4 H, m, S—CH2—CH2), 1.85 (4 H, m, O—CH2—CH2), 2.55 (4 H, q, 3J=7.4, SCH2), 4.07 (4 H, t, 3J=6.5 Hz, OCH2), 7.01 (4 H, d, 3J=8.9 Hz, Ar—H), 7.22 (3 H, m, Ar—H), 7.40 (4 H, d, 3J=8.7 Hz, Ar—H), 7.50 (1 H, t, 3J=8.2 Hz, Ar—H), 8.17 (4 H, d, 3J=8.9 Hz, Ar—H), 8.29 (4 H, d, 3J=8.7 Hz, Ar—H). 13C NMR: δC (CDCl3; 75 MHz): 25.1, 26.4, 28.8, 29.5, 29.7, 29.9, 29.9, 34.4, 53.8, 68.8, 114.8, 116.2, 119.7, 121.4, 122.5, 127.0, 130.3, 132.3, 132.8, 151.8, 155.9, 164.2, 164.5, 164.7. m/z (MALDI) 985.81 [M+Na]+, C56H66NaO10S2 requires 985.40.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 6 hours
  3. extractionextracted with CH2Cl2 (2×200 mL)
  4. customThe solvent was removed
  5. customthe residue purified by column chromatography (CH2Cl2: EtOH, 10:0.03)
  6. customThe product was then selectively precipitated from CH2Cl2 through dropwise addition of petroleum ether

Sources & evidence

ORD record
ord-259ea4529e39445aa7c6b8257e25b618
Source dataset
uspto-grants-2012_01
Patent number
US08092712B2

Reaction notes

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