Triethylamine → HCID 69383080, compound

HRID 722829Notes

Reaction equation

HRID 722829 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]/[C@@H:16]([OH:21])[C@@H:17]([NH2:20])[CH2:18][OH:19].CCN(CC)CC.[CH3:29][C:30]([Si:33](Cl)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH3:32])[CH3:31]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[NH2:20][C@H:17]([C@H:16]([OH:21])[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:18][O:19][Si:33]([C:30]([CH3:32])([CH3:31])[CH3:29])([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 5280335Sphingosine

Product 1

HCID 69383080HCID 69383080, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of D-erythro-sphingosine (46 mg, 0.153 mmol) in CH2Cl2 (1.5 mL) at room temperature, Et3N (32 μL, 0.230 mmol), TBDPSCl (44 μL, 0.169 mmol) and 4-DMAP (ca. 5 mg, cat.) were added. After stirring for 4 h, the reaction was quenched with H2O (10 mL), extracted with EtOAc (3×10 mL), dried over Na2SO4 and concentrated in vacuo. The crude was purified by column chromatography on silica (hexane/EtOAc 5:1 to 100% EtOAc) to obtain 136 as a colorless oil (33 mg, 40% yield).

Workup

  1. customthe reaction was quenched with H2O (10 mL)
  2. extractionextracted with EtOAc (3×10 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified by column chromatography on silica (hexane/EtOAc 5:1 to 100% EtOAc)

Sources & evidence

ORD record
ord-c367ce82c78942b582d6c3c9327c5700
Source dataset
uspto-grants-2006_11
Patent number
US07138547B2

Reaction notes

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