2-Morpholinoethylamine → HCID 53967990, compound

HRID 2256730Notes

Reaction equation

HRID 2256730 reaction equation
[CH:1]([C@@H:4]1[CH2:8][C@@H:7]([C@@H:9]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:10][C@@H:11]([CH:30]([CH3:32])[CH3:31])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][OH:23])=[C:15]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:14]=2)[O:6][C:5]1=[O:41])([CH3:3])[CH3:2].[NH2:42][CH2:43][CH2:44][N:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1>C(O)(=O)C>[O:48]1[CH2:49][CH2:50][N:45]([CH2:44][CH2:43][NH:42][C:5](=[O:41])[C@H:4]([CH:1]([CH3:2])[CH3:3])[CH2:8][C@H:7]([OH:6])[C@@H:9]([NH:33][C:34]([O:36][C:37]([CH3:39])([CH3:40])[CH3:38])=[O:35])[CH2:10][C@@H:11]([CH:30]([CH3:31])[CH3:32])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][OH:23])=[C:15]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:14]=2)[CH2:46][CH2:47]1

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 9873040HCID 9873040, compound

Product 1

HCID 53967990HCID 53967990, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 84 mg of 3(S)-isopropyl-5(S)-{1(S)-tert-butoxycarbonylamino-3(S)-isopropyl-4-[4-(3-hydroxypropyloxy)-3-(3-methoxypropyloxy)-phenyl]-butyl}-tetrahydrofuran-2-one, 0.6 ml of 4-(2-aminoethyl)-morpholine and 0.025 ml of glacial acetic acid is stirred for 16 hours at room temperature and for 6 hours at 45° C. and is then partitioned between diethyl ether (2×) and saturated NaHCO3 solution (1×) and water (2×). The organic phases are combined, dried over magnesium sulfate and concentrated by evaporation, and the residue is purified by means of FC (5 g of silica gel, dichloromethane/methanol=98:2), yielding the title compound: Rf (dichloromethane/methanol=95:5)=0.16; HPLC Rt =14.49 minutes; FAB-MS (M+H)+ =710.

Workup

  1. customis then partitioned between diethyl ether (2×) and saturated NaHCO3 solution (1×) and water (2×)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated by evaporation
  4. customthe residue is purified by means of FC (5 g of silica gel, dichloromethane/methanol=98:2)

Sources & evidence

ORD record
ord-127bfd937b8545db8253488f00c4077f
Source dataset
uspto-grants-1997_08
Patent number
US05654445

Reaction notes

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