Water → HCID 131728269, compound

HRID 500298Notes

Reaction equation

HRID 500298 reaction equation
C(N(CC)C(C)C)(C)C.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[CH3:16][N:17]([C:32](OC1C=CC([N+]([O-])=O)=CC=1)=[O:33])[C@H:18]([C:20]([C@:22]([CH3:31])([OH:30])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:21])[CH3:19].O>C(Cl)Cl>[CH3:16][N:17]([C:32]([N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:33])[C@H:18]([C:20]([C@:22]([CH3:31])([OH:30])[C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])=[O:21])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 131728270HCID 131728270, compound

Product 1

HCID 131728269HCID 131728269, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.65 g (5.0 mmol) of N,N-diisopropylethylamine (“Hünig's base”) and 0.45 g (5.0 mmol) of morpholine are added at room temperature to a solution of 2.0 g (5.0 mmol) of tert-butyl N-methyl-N-(4-nitro-phenoxy)carbonyl-L-alanyl-D-lactate in 40 ml of methylene chloride, and the mixture is stirred at reflux temperature for 18 hours. During the course of this a strong yellow colouration of the reaction mixture occurs. The reaction solution is shaken twice with water, and the organic phase is separated off and concentrated in vacuo after drying over sodium sulphate. The residual crude product is chroratographed on a silica gel column (silica gel 60—Merck, particle size: 0.04 to 0.063 mm) using the eluent cyclohexane:ethyl acetate (1:1).

Workup

  1. temperatureat reflux temperature for 18 hours
  2. customthe organic phase is separated off
  3. concentrationconcentrated in vacuo
  4. dry with materialafter drying over sodium sulphate

Sources & evidence

ORD record
ord-05e7c821a19f45dea175a34997a870a8
Source dataset
uspto-grants-2010_08
Patent number
US07772190B2

Reaction notes

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