Methanol → HCID 131720316, compound

HRID 2293883Notes

Reaction equation

HRID 2293883 reaction equation
[C:1]([O:9][C@H:10](/[CH:44]=[CH:45]/[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[C@@H:11]([N:41]=[N+:42]=[N-:43])[CH2:12][O:13][C@H:14]1[O:30][C@H:29]([CH2:31][O:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C@H:19]([O:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:17]([OH:18])[C@H:15]1[OH:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:59](Cl)(=[O:66])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1.[CH3:68][OH:69]>N1C=CC=CC=1.C(Cl)Cl>[C:1]([O:9][C@H:10](/[CH:44]=[CH:45]/[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[C@@H:11]([NH:41][C:68](=[O:69])[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:10][CH2:11][CH3:12])[CH2:12][O:13][C@H:14]1[O:30][C@H:29]([CH2:31][O:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C@H:19]([O:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:17]([OH:18])[C@H:15]1[O:16][C:59](=[O:66])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:1]([O:9][C@H:10](/[CH:44]=[CH:45]/[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[C@@H:11]([N:41]=[N+:42]=[N-:43])[CH2:12][O:13][C@H:14]1[O:30][C@H:29]([CH2:31][O:32][CH2:33][C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[C@H:19]([O:20][CH2:21][C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])[C@H:17]([O:18][C:68](=[O:69])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@H:15]1[O:16][C:59](=[O:66])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 7412Benzoyl chlorideHCID 131720317HCID 131720317, compound

Product 2

HCID 86751606HCID 86751606, compoundHCID 131720316HCID 131720316, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

A solution of (2S,3R,4E)-3-benzoyloxy-2-azido-1-(4,6-di-O-tert-butyloxycarbonylmethyl-α-D-galactopyranosyloxy)-4-octadecene prepared as described in Example 1-E (0.422 g, 0.51 mmol) in pyridine (12 mL) and methylene chloride (12 mL) was treated with benzoyl chloride (80 μL, 0.69 mmol) at -15° C. The mixture was stirred for 30 minutes at -15° C. then methanol (10 mL) was added and the mixture was stirred for another 18 hours at room temperature. The solvents were evaporated and the residue was co-evaporated with toluene (2×5 mL) and diluted with ethyl acetate (100 mL). This organic phase was washed with 1M aqueous sodium bicarbonate (2×100 mL), water (2×100 mL) and brine (2×100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (60g, 5 to 20% ethyl acetate/hexane) and afforded the title compound (0.420 g, 90%) along with (2S,3R,4E)-3-benzoyloxy-2-azido-1-(2,3-di-O-benzoyl-4,6-di-O-tert-butyloxycarbonylmethyl-α-D-galactopyranosyloxy)-4-octadecene (0.028g).

Workup

  1. stirringthe mixture was stirred for another 18 hours at room temperature
  2. customThe solvents were evaporated
  3. additiondiluted with ethyl acetate (100 mL)
  4. washThis organic phase was washed with 1M aqueous sodium bicarbonate (2×100 mL), water (2×100 mL) and brine (2×100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (60g, 5 to 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b41dde89091a4f258719e89e2507947a
Source dataset
uspto-grants-1997_11
Patent number
US05686426

Reaction notes

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