2-Morpholinoethanol → HCID 136436875, compound

HRID 990234Notes

Reaction equation

HRID 990234 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[OH:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(O[C:23]1[C:28]([C:29]2[NH:30][C:31](=[O:48])[C:32]3[C:33](=[C:35]([CH2:45][CH2:46][CH3:47])[N:36]([CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=4)[N:37]=3)[N:34]=2)=[CH:27][C:26]([S:49]([N:52]2[CH2:57][CH2:56][N:55]([CH2:58][CH3:59])[CH2:54][CH2:53]2)(=[O:51])=[O:50])=[CH:25][N:24]=1)C>>[CH2:58]([N:55]1[CH2:56][CH2:57][N:52]([S:49]([C:26]2[CH:27]=[C:28]([C:29]3[NH:30][C:31](=[O:48])[C:32]4[C:33](=[C:35]([CH2:45][CH2:46][CH3:47])[N:36]([CH2:38][C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=5)[N:37]=4)[N:34]=3)[C:23]([O:11][CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[N:24][CH:25]=2)(=[O:51])=[O:50])[CH2:53][CH2:54]1)[CH3:59]

Participants

4

Reactant 3

HCID 611632-MorpholinoethanolHCID 3251421Potassium bis(trimethylsilyl)amideHCID 135485687HCID 135485687, compound

Product 1

HCID 136436875HCID 136436875, compoundYield 30%

Conditions

Temperature
100 °C

Procedure

A mixture of potassium bis(trimethylsilyl)amide (180 mg, 0.88 mmol) and 4-(2-hydroxyethyl)morpholine (4 ml) was stirred at 100° C. for 1 hour, then the title compound of Example 26 (100 mg, 0.17 mmol) added and the reaction mixture stirred at 110° C. for 18 hours. The resulting, cool mixture was partitioned between water (10 ml) and dichloromethane (20 ml), the phases separated and the organic phase washed with water (10 ml), dried (MgSO4) and evaporated under reduced pressure. The residual yellow oil was purified by column chromatography on silica gel, using an elution gradient of ethyl acetate:methanol (90:10 to 80:20), to yield the title compound (33 mg, 30%) as a white solid. δ (CDCl3): 0.95 (3H, t), 1.04 (3H, t), 1.74 (2H, m), 2.42 (2H, q), 2.56 (4H, m), 2.64 (4H, m), 2.90 (2H, t), 2.99 (2H, t), 3.15 (4H, m), 3.80 (4H, m), 4.75 (2H, t), 5.68 (2H, s), 7.12 (1H, d), 7.25 (1H, m), 7.63 (1H, m), 8.58 (1H, d), 8.62 (1H, s), 8.92 (1H, s), 11.16 (1H, s). LRMS: m/z 652 (M+1)+.

Workup

  1. stirringthe reaction mixture stirred at 110° C. for 18 hours
  2. temperatureThe resulting, cool mixture
  3. customwas partitioned between water (10 ml) and dichloromethane (20 ml)
  4. customthe phases separated
  5. washthe organic phase washed with water (10 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customThe residual yellow oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4427914dbd994e159371d48f75d0a17e
Source dataset
uspto-grants-2002_10
Patent number
US06458951B2

Reaction notes

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