Triethylamine → HCID 89498393, compound

HRID 1778824Notes

Reaction equation

HRID 1778824 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:26]([C:36]3[CH:37]=[N:38][N:39]([CH2:41][C:42]4[CH:47]=[CH:46][C:45]([O:48][CH2:49][C:50]5[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=5)=[CH:44][CH:43]=4)[CH:40]=3)=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12].Cl[CH2:57][O:58][CH2:59][CH2:60][Si:61]([CH3:64])([CH3:63])[CH3:62].C(N(CC)CC)C>O1CCCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:57][O:58][CH2:59][CH2:60][Si:61]([CH3:64])([CH3:63])[CH3:62])[C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[C:26]([C:36]3[CH:37]=[N:38][N:39]([CH2:41][C:42]4[CH:43]=[CH:44][C:45]([O:48][CH2:49][C:50]5[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=5)=[CH:46][CH:47]=4)[CH:40]=3)=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 89497995HCID 89497995, compound

Product 1

HCID 89498393HCID 89498393, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of EXAMPLE 4C (0.30 g) and (2-(chloromethoxy)ethyl)trimethylsilane (0.094 g) in tetrahydrofuran (4 mL) was treated with triethylamine (0.122 g) at room temperature. The reaction was stirred for 1 hour. The reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 5% ethyl acetate in hexanes to provide the title compound.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. extractionThe aqueous layer was extracted with additional ethyl acetate twice
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel eluting with 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c3306bafe97d4cdab1c14246d822164a
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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