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Triethylamine → HCID 86701115, compound

HRID 1396273
Notes
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Reaction equation

HRID 1396273 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:17]([CH2:18][OH:19])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:20]([CH3:22])[CH3:21])[S:14]2)[C@H:10]1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][S:32](Cl)(=[O:34])=[O:33].C(N(CC)CC)C>ClCCl>[CH3:31][S:32]([O:19][CH2:18][C@H:17]1[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:20]([CH3:22])[CH3:21])[S:14]2)[C@@H:10]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@@H:9]1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:34])=[O:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69081709HCID 69081709, compound

Product 1

HCID 86701115HCID 86701115, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ((3aR,5R,6S,7R,7aR)-6,7-bis(benzyloxy)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)methanol (94) (8 g, 18 mmol) (Prepared according to the synthesis of Example 149, step 2) in dichloromethane (50 mL) was added methanesulfonyl chloride (4.3 g, 37 mmol) and triethylamine (3.8 g, 37 mmol) at 0° C. After kept 2 hours at 25° C., the reaction was quenched by water (50 mL) and extracted with dichloromethane (3×50 mL). The combined organic layer was washed with brine (2×30 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a residue, which was purified by a silica gel column, eluted with 20%-30% ethyl acetate in petroleum ether to afford the title compound as a brown syrup (8.5 g, 90%); (ES, m/z) [M+H]+ 507.0; 1HNMR (300 MHz, CDCl3) δ 7.28-7.48 (m, 10H), 6.38 (d, J=6.6 Hz, 1H), 5.04-5.08 (m, 1H), 4.72-4.86 (m, 4H), 4.19-4.24 (m, 3H), 3.70-3.83 (m, 1H), 3.56-3.58 (m, 1H), 3.19 (s, 3H), 2.94 (s, 6H).

Workup

  1. customthe reaction was quenched by water (50 mL)
  2. extractionextracted with dichloromethane (3×50 mL)
  3. washThe combined organic layer was washed with brine (2×30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a residue, which
  8. customwas purified by a silica gel column
  9. washeluted with 20%-30% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-d277415514954d9a85e91a215fbaa9b4
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08901087B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes