Sodium Chloride → HCID 11963978, compound

HRID 1012857Notes

Reaction equation

HRID 1012857 reaction equation
[CH:1]([C@H:4]1[NH:19][C:18](=[O:20])[C@@H:17]([CH2:21][S:22]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[NH:16][C:15](=[O:42])[C@@H:14]([CH3:43])[NH:13][C:12](=[O:44])[CH2:11][C@@H:10](/[CH:45]=[CH:46]/[CH2:47][CH2:48][S:49]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:9][C:8](=[O:69])[CH2:7][NH:6][C:5]1=[O:70])([CH3:3])[CH3:2].S([O-])([O-])(=O)=S.[Na+].[Na+].[Na+].[Cl-]>C(Cl)Cl.CO>[CH:1]([C@H:4]1[NH:19][C:18](=[O:20])[C@@H:17]2[NH:16][C:15](=[O:42])[C@@H:14]([CH3:43])[NH:13][C:12](=[O:44])[CH2:11][C@@H:10]([CH:45]=[CH:46][CH2:47][CH2:48][S:49][S:22][CH2:21]2)[O:9][C:8](=[O:69])[CH2:7][NH:6][C:5]1=[O:70])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 24477Sodium ThiosulfateHCID 23656940HCID 23656940, compound

Product 1

HCID 11963978HCID 11963978, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a vigorously stirring solution of 12 (1120 mg, 4.42 mmol) in CH2Cl/MeOH (9:1, 1000 mL) was added the protected dithiol 8A (430 mg, 0.44 mmol) in CH2Cl2/MeOH (9:1, 500 mL) dropwise over 30 minutes. After stirring for a further 30 minutes, 0.1M sodium thiosulfate (300 mL) and sat. NaCl (100 mL) were added, extracting with CH2Cl2 (3×100 mL). The combined organic extract was dried (MgSO4), filtered, and solvent removed. The residue was purified by flash chromatography (eluent 1-6% MeOH/CH2Cl2) to give 9A (205 mg, 0.42 mmol, 96%) as a white solid: [α]22D −98.0 (c 0.50, CHCl3); IR νmax 3300, 2477, 1734, 1659, 1526, 1446 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.46 (d, J=6.5 Hz, 1H), 7.33 (t, J=5.3 Hz, 1H), 7.28 (d, J=8.8 Hz, 1H), 6.60 (d, J=3.8 Hz, 1H), 5.95 (dtd, J=16.1, 6.5, 2.0 Hz, 1H), 5.80-5.70 (m, 2H), 4.85 (ddd, J=9.8, 8.5, 3.8 Hz, 1H), 4.21 (qd, J=7.3, 3.8 Hz, 1H), 4.11 (d, J=5.3 Hz, 2H), 3.44 (dd, J=15.6, 10.0 Hz, 1H), 3.20 (dd, J=10.3, 6.8 Hz, 1H), 3.01-2.95 (m, 2H), 2.92 (dd, J=15.6, 4.0 Hz, 1H), 2.85-2.58 (m, 5H) 1.49 (d, J=7.5 Hz, 3H), 0.98 (d, J=6.5 Hz, 3H), 0.92 (d, J=6.5 Hz, 3H); 13C NMR 100 MHz 173.3 (C), 171.6 (C), 171.0 (C), 169.4 (C), 168.2 (C), 130.4 (CH), 130.3 (CH), 69.8 (CH), 64.9 (CH), 54.5 (CH), 52.0 (CH), 42.4 (2×CH2), 38.7 (CH2), 38.6 (CH2), 32.7 (CH2), 27.5 (CH), 20.8 (CH3), 20.1 (CH3), 16.7 (CH3); LRMS (ES+) m/z 995 (50%, [2M+Na]+), 509 (80%, [M+Na]+), 487 (100%, [M+H]+); HRMS m/z 509.1495 (M+Na)+ expected 509.1499.

Workup

  1. extractionextracting with CH2Cl2 (3×100 mL)
  2. extractionThe combined organic extract
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. customsolvent removed
  6. customThe residue was purified by flash chromatography (eluent 1-6% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-014f76a02faf470da3568f38a2d1d29e
Source dataset
uspto-grants-2011_07
Patent number
US07977304B2

Reaction notes

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