Methanol → HCID 86684842, compound

HRID 537835Notes

Reaction equation

HRID 537835 reaction equation
[CH3:1][N:2]([CH3:63])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH:9]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]/[CH:53]=[CH:54]\[CH2:55]/[CH:56]=[CH:57]\[CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][C@H:21]([O:27][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:7].CO.C(Cl)Cl>Cl>[CH3:63][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH:9]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]/[CH:53]=[CH:54]\[CH2:55]/[CH:56]=[CH:57]\[CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][C@H:21]([OH:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 6344DichloromethaneHCID 86684843HCID 86684843, compound

Product 1

HCID 86684842HCID 86684842, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (6R,8Z,27Z,30Z)-6-(tert-butyldiphenylsilyloxy)hexatriaconta-8,27,30-trien-18-yl 4-(dimethylamino)butanoate (800 mg, 0.95 mmol) in the saturated HCl(g)/MeOH (50 mL) was stirred for 10 minutes. The starting material did not dissolve so anhydrous DCM (12 mL) was added, and the mixture was stirred for 30 minutes. Upon completion, the solution was concentrated in vacuo, saturated sodium bicarbonate (75 mL) was added, and the solution was extracted with ethyl acetate (3×100 mL). The combined ethyl acetate extracts were washed with brine (100 mL), dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography (100% ethyl acetate) to afford the title compound as a colorless oil (0.228 g, 39%). 1H NMR (400 MHz, CDCl3): δ5.61-5.52 (m, 1H), 5.45-5.29 (m, 4H), 4.91-4.83 (m, 1H), 3.66-3.58 (m, 1H), 2.81-235 (m, 2H), 2.75-2.44 (m, 7H), 2.42-2.36 (m, 2H), 2.24-2.18 (m, 2H), 2.10-1.93 (m, 7H), 1.56-1.41 (m, 6H), 1.40-1.20 (m, 36H), 0.93-0.85 (m, 6H).

Workup

  1. additionwas added
  2. concentrationUpon completion, the solution was concentrated in vacuo, saturated sodium bicarbonate (75 mL)
  3. additionwas added
  4. extractionthe solution was extracted with ethyl acetate (3×100 mL)
  5. washThe combined ethyl acetate extracts were washed with brine (100 mL)
  6. customdried on magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to dryness
  9. customThe residue was purified by column chromatography (100% ethyl acetate)

Sources & evidence

ORD record
ord-8aef8621f54648769f8ad855374bc013
Source dataset
uspto-grants-2014_10
Patent number
US08865675B2

Reaction notes

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